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[ CAS No. 54-85-3 ] {[proInfo.proName]}

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Chemical Structure| 54-85-3
Chemical Structure| 54-85-3
Structure of 54-85-3 * Storage: {[proInfo.prStorage]}
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Product Details of [ 54-85-3 ]

CAS No. :54-85-3 MDL No. :MFCD00006426
Formula : C6H7N3O Boiling Point : -
Linear Structure Formula :- InChI Key :QRXWMOHMRWLFEY-UHFFFAOYSA-N
M.W : 137.14 Pubchem ID :3767
Synonyms :
INH;Isonicotinic acid hydrazide;Isoniazid, Isonicotinylhydrazide, Hydra, Hyzyd, Isovit, Nydrazid;NSC 9659;Isonicotinylhydrazide;Isonicotinic hydrazide

Calculated chemistry of [ 54-85-3 ]

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 2
Num. H-bond acceptors : 3.0
Num. H-bond donors : 2.0
Molar Refractivity : 35.13
TPSA : 68.01 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -7.63 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.03
Log Po/w (XLOGP3) : -0.7
Log Po/w (WLOGP) : -0.31
Log Po/w (MLOGP) : -0.47
Log Po/w (SILICOS-IT) : -0.27
Consensus Log Po/w : -0.35

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -0.56
Solubility : 37.7 mg/ml ; 0.275 mol/l
Class : Very soluble
Log S (Ali) : -0.25
Solubility : 76.6 mg/ml ; 0.558 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -1.64
Solubility : 3.17 mg/ml ; 0.0231 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.24

Safety of [ 54-85-3 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P264-P270-P280-P301+P312+P330-P302+P352-P332+P313-P362+P364-P501 UN#:N/A
Hazard Statements:H302-H315 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 54-85-3 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Upstream synthesis route of [ 54-85-3 ]
  • Downstream synthetic route of [ 54-85-3 ]

[ 54-85-3 ] Synthesis Path-Upstream   1~28

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Reference: [1] Chemistry Letters, 2010, vol. 39, # 6, p. 546 - 547
  • 2
  • [ 67-56-1 ]
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  • [ 55-22-1 ]
  • [ 2459-09-8 ]
Reference: [1] Journal of Chemical Research - Part S, 1996, # 2, p. 100 - 101
  • 3
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  • [ 2564-83-2 ]
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  • [ 1020092-80-1 ]
Reference: [1] Organic and Biomolecular Chemistry, 2013, vol. 11, # 1, p. 170 - 176
[2] Organic and Biomolecular Chemistry, 2013, vol. 11, # 1, p. 170 - 176
  • 4
  • [ 1570-45-2 ]
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YieldReaction ConditionsOperation in experiment
86% With hydrazine hydrate In ethanol at 60℃; for 1 h; Commercially available ethyl isonicotinate was refluxed with hydrazine hydrate. for 1 hr at 60° C. and the solvent was evaporated. Trituration of this solid with diethyl ether afforded pure hydrazide 2 in 86percent yield. The treatment of hydrazide 2 with CS2 and KOH in 60 ° C. for 18 hrs produced a solid upon concentration in vacuo. It was found that this material could be easily purified by trituration with H20 followed by filtration to give thiol 3 in 78percent yield, thus avoiding chromatography over the first two steps. This operationally simple procedure afforded multi-gram quantities of 3 for subsequence focused library synthesis. Finally, diversification of the aryl ring was achieved by nucleophilic displacement reaction of thiol 3 with substituted aryl bromides in room temperature DMF using K2C03 as base.
86% With hydrazine hydrate In ethanol at 60℃; for 1 h; Commercially available ethyl isonicotinate was refluxed with hydrazine hydrate for 1 hr at 60° C. and the solvent was evaporated. Trituration of this solid with diethyl ether afforded pure hydrazide 2 in 86percent/o yield. The treatment of hydrazide 2 with CS2 and KOH in 60° C. for 18 hrs produced a solid upon concentration in vacuo. It was found that this material could be easily purified by trituration with H2O followed by filtration to give thiol 3 in 78percent yield, thus avoiding chromatography over the first two steps. This operationally simple procedure afforded multi-gram quantities of 3 for subsequence focused library synthesis. Finally, diversification of the aryl ring was achieved by nucleophilic displacement reaction of thiol 3 with substituted aryl bromides in room temperature DMF using K2CO3 as base.
86% With hydrazine hydrate In ethanol for 10.25 h; Cooling with ice; Reflux Isonicotinicacid ethyl ester 1 (1.5g, 10mmol) was dissolved in 15mL of ethanol, then under ice-cooling was slowly added dropwise with hydrazine hydrate (2g, 40mmol), after the addition was complete, it was stirred at room temperature for 15min, then heated under reflux for 10h. After completion of the reaction, ethanol was removed by rotary evaporation, poured into water, extracted with ethyl acetate, the organic phase was dried and concentrated to give the desired product 2 (1.2g, 86percent), without purification into the next step.
85% With hydrazine hydrate In ethanol for 24 h; Reflux Step 1: 15.12 g (0.1 mol) of ethyl pyridine-4-carboxylate and 10.00 g (0.2 mol) of hydrazine hydrate (NH 2 NH 2 · H 2 O) were added to 50 mL of ethanol, refluxed for 24 h, cooled to room temperature, and the solution was spun dry and recrystallized. The 11.62 g (0.085 mol) pyridine-4-formyl hydride was obtained in a yield of 85percent.
73% With hydrazine hydrate In ethanol for 6 h; Reflux To a solution of ethyl isonicotinate (1.44 g, 10 mmol) inEtOH (10 mL), 85percent hydrazine hydrate (2 mL, 35 mmol)was added dropwise. The mixture was heated under refluxfor 6 h. After the reaction was over, the mixture was cooledto room temperature, filtered, washed with cool ethyl acetate,and then dried to give white solid isonicotinyi hydrazine 2,yield (1.0 g, 73percent).
73% With hydrazine hydrate In water for 6 h; A mixture of ethyl isonicotinate (1.44 g, 10 mmol) and 85percent hydrazine hydrate (2 mL, 35 mmol) was heated under reflux for 6 h. The mixture was cooled to room temperature,filtered, washed with cool ethyl acetate, then dried to give white solid isonicotinohydrazide 2. Yield 1.0 g, 73percent.
12.9 g With hydrazine hydrate In ethanol for 3 h; Reflux General procedure: An ethanol (300 ml) suspension of salicylic acid(13.8 g; 0.1 mol) and strongly acidic ion-exchange resin,Amberlyst-15 (5 g) were stirred with refluxing for three days.Insoluble catalyst was separated by filtration, and washed withethanol (3 20 ml). Combined ethanol filtrates were mixed with hydrazine hydrate (20 ml; 20.5 g; 0.4 mol) and refluxed with slowsolvent distillation using the modified Hickman still apparatus(Scheme 3). After 3 h of refluxing, the volume of the reaction mixturewas reduced to about 50 ml and white precipitate started toform. The white suspension was cooled to room temperature andthen left at 5 C for 1 h. Insoluble product was separated by filtration,washed with ice cold ethanol, and dried on air to give pureproduct (13.2 g; 87percent).

Reference: [1] Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2015, vol. 54B, # 10, p. 1260 - 1274
[2] Bioorganic and Medicinal Chemistry Letters, 2014, vol. 24, # 6, p. 1532 - 1537
[3] Patent: US2015/210679, 2015, A1, . Location in patent: Paragraph 0091
[4] Patent: US2016/214969, 2016, A1, . Location in patent: Paragraph 0076-0077
[5] Patent: CN105481765, 2016, A, . Location in patent: Paragraph 0030; 0031; 0032
[6] Patent: CN104892639, 2018, B, . Location in patent: Paragraph 0052; 0053; 0054; 0066; 0067; 0068; 0069
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[8] Medicinal Chemistry Research, 2013, vol. 22, # 10, p. 4953 - 4963
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[11] Monatshefte fuer Chemie, 1912, vol. 33, p. 403
[12] Acta Chimica Academiae Scientiarum Hungaricae, 1958, vol. 14, p. 197,199
[13] Chimica, 1952, vol. 7, p. 229
[14] Roczniki Chemii, 1953, vol. 27, p. 161,163[15] Chem.Abstr., 1954, p. 13688
[16] Yakugaku Zasshi, 1951, vol. 71, p. 1002[17] Chem.Abstr., 1952, p. 8120
[18] Journal of the American Pharmaceutical Association (1912-1977), 1956, vol. 45, p. 478
[19] Pharm. Ind., 1952, vol. 14, p. 366
[20] European Journal of Medicinal Chemistry, 1990, vol. 25, # 1, p. 75 - 79
[21] European Journal of Medicinal Chemistry, 2006, vol. 41, # 7, p. 841 - 846
[22] Phosphorus, Sulfur and Silicon and the Related Elements, 2006, vol. 181, # 9, p. 2079 - 2087
[23] Chemistry of Heterocyclic Compounds, 2006, vol. 42, # 2, p. 233 - 245
[24] European Journal of Medicinal Chemistry, 2009, vol. 44, # 8, p. 3340 - 3344
[25] Journal of Medicinal Chemistry, 2009, vol. 52, # 14, p. 4200 - 4209
[26] Bioorganic and Medicinal Chemistry, 2010, vol. 18, # 11, p. 4042 - 4048
[27] European Journal of Medicinal Chemistry, 2010, vol. 45, # 9, p. 3943 - 3949
[28] European Journal of Medicinal Chemistry, 2010, vol. 45, # 9, p. 3960 - 3969
[29] Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2010, vol. 49, # 4, p. 526 - 531
[30] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 24, p. 7246 - 7250
[31] Medicinal Chemistry Research, 2012, vol. 21, # 7, p. 1451 - 1470
[32] Medicinal Chemistry Research, 2012, vol. 21, # 8, p. 1935 - 1952,18
[33] Medicinal Chemistry Research, 2012, vol. 21, # 8, p. 1935 - 1952
[34] Journal of the Chemical Society of Pakistan, 2018, vol. 40, # 2,
[35] Medicinal Chemistry Research, 2012, vol. 21, # 11, p. 3646 - 3655
[36] Medicinal Chemistry, 2013, vol. 9, # 1, p. 53 - 76
[37] Bioorganic and Medicinal Chemistry, 2013, vol. 21, # 8, p. 2286 - 2297
[38] European Journal of Medicinal Chemistry, 2015, vol. 102, p. 243 - 248
[39] Bioorganic Chemistry, 2018, vol. 80, p. 253 - 260
[40] ACS Medicinal Chemistry Letters, 2013, vol. 4, # 11, p. 1097 - 1101
[41] European Journal of Medicinal Chemistry, 2014, vol. 71, p. 199 - 218
[42] Dyes and Pigments, 2014, vol. 108, p. 32 - 40
[43] Archives of Pharmacal Research, 2014, vol. 37, # 7, p. 852 - 861
[44] Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 13, p. 3397 - 3407
[45] Medicinal Chemistry Research, 2015, vol. 24, # 12, p. 4166 - 4180
[46] Transition Metal Chemistry, 2015, vol. 40, # 6, p. 665 - 671
[47] Polyhedron, 2016, vol. 106, p. 138 - 143
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[49] Inorganica Chimica Acta, 2017, vol. 461, p. 301 - 315
[50] ChemMedChem, 2017, vol. 12, # 12, p. 972 - 985
[51] Patent: CN107011255, 2017, A, . Location in patent: Paragraph 0024
[52] Chemistry and Biodiversity, 2018, vol. 15, # 9,
[53] Patent: CN105085390, 2018, B, . Location in patent: Paragraph 0059-0067
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YieldReaction ConditionsOperation in experiment
94.1% With hydrazine hydrate In ethanol at 20℃; for 3 h; Methyl 4-picolinate (2.74 g, 20 mmol) and absolute ethanol (15 mL) were added to a 50 mL round bottom flask,Stir at room temperature until the solid dissolves completely.Slowly drip hydrated hydrazine (30mmol 100percent),A large number of needle-like white solids appeared immediately after the addition.After stirring at room temperature for 3 hours, it was filtered, rinsed with a small amount of ethanol, and dried in vacuo to give 2.58 g of white needles, yield 94.1percent,
86% With hydrazine hydrate In ethanol at 23℃; for 16 h; i) A solution of methyl isonicotinate (1.00 mL, 8.47 mmol) and hydrazine hydrate (1 .23 mL, 25.4 mmol) inethanol (10 mL) was stirred at RT for 16 h. Concentration and subsequent coevaporation with tolueneand DCM gave INT-28A (1.00 g, 7.31 mmol, 86percent). LCMS: caic. for [M+H]=138.07, found 138.1.
78% With hydrazine hydrate In methanol for 5 h; Reflux General procedure: To a solution of an appropriate methyl esters17(a–j) (1.0 mmol) in 50 mL of methanol was added 99 percenthydrazine hydrate (4.0 mmol) and the mixture was refluxedfor 5 h up to reaction completed (TLC). After completionof reaction, it was allowed to cool and the obtained solidwas washed with methanol. The crude products wererecrystallized from ethanol.
75% With hydrazine hydrate In ethanol at 150℃; for 0.0833333 h; Microwave irradiation [00445] To a solution of methyl isonicotinate (100 mg, 0.73 mmol) in 0.3 mL of ethanol was added hydrazine hydrate (0.35 mL, 7.29 mmol). This reaction mixture was heated in a microwave reactor for 5 min at 150°C. The reaction was allowed to cool to room temperature and diluted with 10 mL of MeOH, then concentrated. The residue was purified by column chromatography with MeOH/CH2Cl2 (1 :4) to afford 84 mg (75percent) of the title compound. XH NMR (MeOD) 58.70 (dd, J = 4.8, 1.6 Hz, 2H), 7.77 (dd, J = 4.4, 1.6 Hz, 2H). LRMS calculated for C6H7N30 (M+H)Vz: 137.05 Measured 137.1 m/z.
75% With hydrazine hydrate In ethanol at 150℃; for 0.0833333 h; Microwave irradiation a. PREPARATION OF ISONICOTINOHYDRAZIDE [00471] To a solution of methyl isonicotinate (100 mg, 0.73 mmol) in 0.3 mL of ethanol was added hydrazine hydrate (0.35 mL, 7.29 mmol). This reaction mixture was heated in a microwave reactor for 5 min at 150 °C. The reaction was allowed to cool to room temperature and diluted with 10 mL of MeOH, then concentrated. The residue was purified by column chromatography with MeOH/CH2Cl2 (1:4) to afford 84 mg (75percent) of the desired product. lH NMR (MeOD) δ 8.70 (dd, J = 4.8, 1.6 Hz, 2H), 7.77 (dd, J = 4.4, 1.6 Hz, 2H). LRMS calculated for C6H7N30 (M+H)Vz: 137.05 Measured 137.1 m/z.
73% for 6 h; Reflux Formula (II) (1.37g, 10mmol) and a concentration of 80percent by mass aqueous solution of hydrazine hydrate (2mL, 35mmol) was heated at reflux for 6h, cooled to room temperature, filter, the filter cake was washed with ethyl acetate and dried to give isoniazid as shown in formula (III) in a yield (1.0 g, 73percent).

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[2] Patent: WO2015/161928, 2015, A1, . Location in patent: Page/Page column 48
[3] Medicinal Chemistry Research, 2016, vol. 25, # 4, p. 627 - 643
[4] Patent: WO2016/154471, 2016, A1, . Location in patent: Paragraph 00445
[5] Patent: WO2017/11466, 2017, A1, . Location in patent: Paragraph 00471
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[7] Patent: CN106699776, 2017, A, . Location in patent: Paragraph 0024-0025; 0027; 0030-0031
[8] Arzneimittel-Forschung/Drug Research, 2011, vol. 61, # 8, p. 452 - 457
[9] Bioorganic and Medicinal Chemistry, 2012, vol. 20, # 11, p. 3615 - 3621
[10] Journal of Medicinal Chemistry, 2012, vol. 55, # 9, p. 4407 - 4424
[11] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 16, p. 5185 - 5189
[12] Patent: WO2012/154403, 2012, A2, . Location in patent: Page/Page column 254-255
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YieldReaction ConditionsOperation in experiment
90.4% With hydrazine dihydrochloride In aq. phosphate buffer at 30℃; for 1 h; Enzymatic reaction Fed-batch biotransformation was carried out in 250ml Erlenmeyer flask containing 50ml of reaction mixture with initial isonicotinamide and hydrazine–2HCl concentration of 100 and 1000mM respectively in phosphate buffer (100mM, pH 7) at 30°C and 2.0mgdcw/ml resting cells of B. smithii strain IITR6b2. Powdered isonicotinamide (0.61g) and highly concentrated solution (1ml, 5M, pH 7) of hydrazine–2HCl were fed in subsequent seven feeds at an interval of 60min to restrict the residual isonicotinamide and hydrazine–2HCl concentration above 100 and 1000mM respectively. 500μl of sample was withdrawn at every 30min during the reaction and monitored for isoniazid, isonicotinic acid and isonicotinamide concentration. Effort was made to maintain the reaction volume constant around 50ml. A control experiment was also conducted with same parameters without enzyme for any spontaneous chemical reaction
Reference: [1] Journal of Molecular Catalysis B: Enzymatic, 2013, vol. 97, p. 67 - 73
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YieldReaction ConditionsOperation in experiment
97.34% at 115℃; for 4 h; [00024] 9.9918 gms of isonicotinamide was dissolved in 77.97 gms of absolute alcohol and 10.1 gms of hydrazine hydrate(100percent) was added to it. The reaction mixture was refluxed in glycerine bath for 4 hours at 115 degree Celsius; after which alcohol was distilled off and solid mass, Isonicotinic acid hydrazide (INH) was taken out in hot condition Recovered Isonicotinic acid hydrazide was 9.727 gms i.e. 97.34 wt percent and the melting point obtained was 170° C. against 169.9° C. actual.
97.34% at 115℃; for 4 h; Heating / reflux 9.9918 gms of isonicotinamide was dissolved in 77.97 gms of absolute alcohol and 10.1 gms of hydrazine hydrate (100percent) was added to it. The reaction mixture was refluxed in glycerine bath for 4 hours at 115 degree Celsius; after which alcohol was distilled off and solid mass, Isonicotinic acid hydrazide (INH) was taken out in hot condition. Recovered Isonicotinic acid hydrazide was 9.727 gms i. e. 97.34 wtpercent and the melting point obtained was 170°C against 169. 9°C actual.
96.03% With hydrazine In methanol at 110℃; for 4 h; [00025] 19.3989 gins of isonicotinamide was dissolved in 39.488 gms of methyl alcohol and 14.14 gms of hydrazine hydrate (100percent) was added to it. The reaction mixture was refluxed in glycerine bath for 4 hours at 110 degree Celsius; after which alcohol was distilled off and solid mass, Isonicotinic acid hydrazide (INH) was taken out in hot condition. Recovered Isonicotinic acid hydrazide was 19.3 gms i.e. 99.49 wt percent and the melting point obtained was 169.9° C. against 170° C. actual.EXAMPLE-3 [00026] 24.99 gms of isonicotinamide was dissolved in 39.48 gms of methyl alcohol and 20.20 gms of hydrazine hydrate(100percent) was added to it. The reaction mixture was refluxed in glycerine bath for 4 hours at 110 degree Celsius; after which alcohol was distilled off and solid mass, Isonicotinic acid hydrazide(INH) was taken out in hot condition. Recovered Isonicotinic acid hydrazide was 24.0 gms i.e. 96.03 wt percent and the melting point obtained was 169.9° C. against 170° C. actual.
96.03% With hydrazine In methanol at 110℃; for 4 h; Heating / reflux 19.3989 gms of isonicotinamide was dissolved in 39.488 gms of methyl alcohol and 14.14 gms of hydrazine hydrate (100percent) was added to it. The reaction mixture was refluxed in glycerine bath for 4 hours at 110 degree Celsius ; after which alcohol was distilled off and solid mass, Isonicotinic acid hydrazide (INH) was taken out in hot condition. Recovered Isonicotinic acid hydrazide was 19.3 gms i. e. 99.49 wtpercent and the melting point obtained was 169. 9°C against 170°C actual. Example-3 24.99 gms of isonicotinamide was dissolved in 39.48 gms of methyl alcohol and 20.20 gms of hydrazine hydrate (100percent) was added to it. The reaction mixture was refluxed in glycerine bath for 4 hours at 110 degree Celsius; after which alcohol was distilled off and solid mass, Isonicotinic acid hydrazide (INH) was taken out in hot condition. Recovered Isonicotinic acid hydrazide was 24.0 gms i. e. 96.03 wtpercent and the melting point obtained was 169. 9°C against 170°C actual.
129.3 g With butan-2-one azine In water at 160 - 170℃; Green chemistry The isonicotinamide with stirring into 123g,A thermometer and a reflux condenser,The upper part of the receiver is connected with a conduit to absorb ammonia gas;Open the stir,Heating to 160 ~ 170 ,After the isonicotinamide melts into liquid,Butanone with nitrogen 260g and water 90g slowly added to isonicotinamide,Control reaction temperature of 160 ~ 170 ,Will return the condenser outlet temperature control at 75 ~ 80 ,The addition of butanol at the reflux ratio R = 1 ~ 10 and the recovery of ammonia gas;Butanone with nitrogen and water drop time control in 1 ~ 2h,After the completion of the incubation reaction 30min,And then the temperature rose to 180 ° C ~ 190 ° C unreacted butanone nitrogen distillation recovery,Butanone nitrogen recovery after cooling cooling,The solid matter precipitated in the four-necked flask was filtered,washing,After drying, 129.3 g of isoniazid was obtained.

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  • [ 13841-66-2 ]
  • [ 54-85-3 ]
YieldReaction ConditionsOperation in experiment
74.1% With hydrazine hydrate In ethanol for 6 h; Reflux General procedure: The obtained compounds II was dissolved with ethanol (90 mL) and hydrazine hydrate (85percent, 30 mL),then the mixture was heated to reflux for 6 h. After the reaction was completed, ethanol and the excess of hydrazine hydrate were distilled out under a reduced pressure, and a white product was left. The crude product was recrystallized from ethanol to afford white crystals III.
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  • [ 55-22-1 ]
  • [ 54-85-3 ]
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YieldReaction ConditionsOperation in experiment
84% for 3 h; Reflux General procedure: H2La, H2Lb and H2Lc have been prepared by a general procedure: equimolar amounts of isonicotinohydrazide (4-pyridine carboxylic acid hydrazide) and the corresponding aldehyde, 5-bromo-2-hydroxybenzaldehyde, 2-hydroxynaphthaldehyde and 2,4-dihydroxybenzaldehyde respectively, were refluxed in ethanol for 3h and then cooled to ambient temperature. Crystals suitable for X-ray crystallography were obtained by slow evaporation of a dilute ethanolic solution of the compounds.
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