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[ CAS No. 114527-53-6 ]

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Chemical Structure| 114527-53-6
Chemical Structure| 114527-53-6
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Product Details of [ 114527-53-6 ]

CAS No. :114527-53-6 MDL No. :MFCD06739005
Formula : C10H11NO2 Boiling Point : 392.598°C at 760 mmHg
Linear Structure Formula :- InChI Key :N/A
M.W :177.20 g/mol Pubchem ID :13931066
Synonyms :

Safety of [ 114527-53-6 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 114527-53-6 ]

  • Downstream synthetic route of [ 114527-53-6 ]

[ 114527-53-6 ] Synthesis Path-Downstream   1~14

  • 1
  • [ 6480-68-8 ]
  • [ 114527-53-6 ]
YieldReaction ConditionsOperation in experiment
78% With sodium hydroxide; nickel at 20℃; for 1h;
Multi-step reaction with 3 steps 1: thionyl chloride / 16 h / 0 °C / Inert atmosphere; Reflux 2: borane pyridine complex; acetic acid / 16 h / 20 °C / Inert atmosphere 3: lithium hydroxide monohydrate / tetrahydrofuran; methanol; water / 16 h / 20 °C / Inert atmosphere
Multi-step reaction with 3 steps 1: thionyl chloride / 0 °C / Reflux 2: borane pyridine; acetic acid / 20 °C 3: lithium hydroxide monohydrate; water / methanol; tetrahydrofuran / 20 °C
Multi-step reaction with 3 steps 1: thionyl chloride / 24 h / 0 °C / Reflux; Inert atmosphere 2: borane pyridine / 24 h / 0 - 20 °C / Inert atmosphere 3: lithium hydroxide; water / methanol; tetrahydrofuran / 25 h / 20 °C / Inert atmosphere
Multi-step reaction with 3 steps 1: thionyl chloride / 24 h / 0 °C / Inert atmosphere; Reflux 2: borane pyridine / 24 h / 0 - 20 °C / Inert atmosphere 3: lithium hydroxide / methanol; water; tetrahydrofuran / 25 h / 20 °C / Inert atmosphere

  • 2
  • [ 114527-53-6 ]
  • [ 64-17-5 ]
  • [ 67752-37-8 ]
YieldReaction ConditionsOperation in experiment
97% With sulfuric acid; dihydrogen peroxide at 120℃; for 0.583333h;
YieldReaction ConditionsOperation in experiment
With hydrogenchloride at 100℃; unter Druck;
YieldReaction ConditionsOperation in experiment
With hydrogenchloride at 100℃; unter Druck;
YieldReaction ConditionsOperation in experiment
With water; nickel at 150℃; Hydrogenation;
YieldReaction ConditionsOperation in experiment
96% EXAMPLE Approximately 40 ml of hydrochloric acid are added dropwise at from 15 to 25° C. to the solution so obtained in order to adjust the pH to a value of not less than 5.0, thus completing the precipitation of the end product which is filtered, washed in succession with 600 ml of water and 150 ml of acetone and dried under a vacuum at 70° C. for from 15 to 20 hours. 70 g (yield: 96%) of (-)-1,2,3,4-tetrahydroquinoline-3-carboxylic acid having an optical purity of 100% are thus obtained. [α]D =-139° (c=1, HCl N). 1 H-NMR (200 MHz, DMSO-d6 +TFAd, p.p.m.):3.15 (1H,dd,J=11.3 and 17.2 Hz); 3.35 (1H,dd,J=5.3 and 17.2 Hz); 4.39 (2H,s,N--CH2); 4.47 (1H,dd,J=5.3 and 11.3 Hz, N--CH); 7.28 (4H,s,arom.).
96% EXAMPLE Approximately 40 ml of hydrochloric acid are added dropwise at from 15 to 25°C to the solution so obtained in order to adjust the pH to a value of not less than 5.0, thus completing the precipitation of the end product which is filtered, washed in succession with 600 ml of water and 150 ml of acetone and dried under a vacuum at 70°C for from 15 to 20 hours. 70 g (yield: 96%) of (-)-1,2,3,4-tetrahydroquinoline-3-carboxylic acid having an optical purity of 100% are thus obtained. [α]D=-139°(c=1,HCl N). 1H-NMR (200 MHz, DMSO-d6+ TFAd, p.p.m.):3.15 (1H,dd,J=11.3 and 17.2 Hz); 3.35 (1H,dd,J=5.3 and 17.2 Hz); 4.39 (2H,s,N-CH2); 4.47 (1H,dd,J=5.3 and 11.3 Hz, N-CH); 7.28 (4H,s,arom.).
  • 7
  • [ 114527-53-6 ]
  • [ 100-39-0 ]
  • [ 534-17-8 ]
  • [ 177198-80-0 ]
YieldReaction ConditionsOperation in experiment
In <i>N</i>-methyl-acetamide; hexane; dichloromethane 29.f f f 1-Benzyl-3(R,S)-benzyloxycarbonyl-1,2,3,4-tetrahydroquinoline 5.6 g of 1,2,3,4-tetrahydroquinoline-3(R,S)-carboxylic acid (Example 1t)) are stirred in 100 ml of dimethylformamide, with the addition of 12.7 ml of benzyl bromide and 25.1 g of caesium carbonate, at room temperature for 24 h. The concentrated crude product is then purified by means of FC over 250 g of silica gel with a 1:1 mixture of methylene chloride and hexane as the mobile phase. The title compound is obtained: Rf (1:1 mixture of methylene chloride and hexane)=0.31.
  • 8
  • [ 114527-53-6 ]
  • [ 122-59-8 ]
  • C18H17NO4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: 2-phenoxyacetic acid With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate In dichloromethane at 20℃; for 0.5h; Stage #2: (-)-1,2,3,4-tetrahydroquinoline-3-carboxylic acid In dichloromethane for 2h;
  • 9
  • [ 114527-53-6 ]
  • 3-(4-chloro-3,5-dimethylphenoxy)propanal [ No CAS ]
  • (±)-methyl 1-(3-(4-chloro-3,5-dimethylphenoxy)propyl)-1,2,3,4-tetrahydroquinoline-3-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
44% With sodium tris(acetoxy)borohydride In 1,2-dichloro-ethane at 35℃; for 16h; Inert atmosphere;
  • 10
  • [ 114527-53-6 ]
  • 3-(4-chloro-3,5-dimethylphenoxy)propanal [ No CAS ]
  • (±)-1-(3-(4-chloro-3,5-dimethylphenoxy)propyl)-1,2,3,4-tetrahydroquinoline-3-carboxylic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: sodium tris(acetoxy)borohydride / 1,2-dichloro-ethane / 16 h / 35 °C / Inert atmosphere 2: lithium hydroxide monohydrate / tetrahydrofuran; methanol; water / 16 h / 20 °C / Inert atmosphere
  • 12
  • [ 177202-62-9 ]
  • [ 114527-53-6 ]
YieldReaction ConditionsOperation in experiment
43% With lithium hydroxide monohydrate In tetrahydrofuran; methanol; water at 20℃; for 16h; Inert atmosphere;
With lithium hydroxide monohydrate; water In tetrahydrofuran; methanol at 20℃; 4 As depicted in Scheme 4-1, quinoline-3-carboxylic acid 3 was esterified with thionyl chloride in methanol to yield ester 4. Reduction of the pyridine ring of 4 with pyridine-borane complex in glacial acetic acid then delivered racemic THQ 5 whose methyl ester was saponified to yield ±-6. Alternatively, sulfonylation of ±-5 furnished compounds ±-7, which were also saponified with lithium hydroxide to afford the 3-carboxy target compounds ±-8. Further elaboration of the phenylsulfonyl group in ±-7c was accomplished by an SNAr reaction with 4- chloro-3,5-dimethylphenol followed by ester hydrolysis to afford compound ±-2, as shown in Scheme 4-2. In addition, the phenylsulfonyl moiety in ±-2 was replaced with a more flexible propylene group through a reductive amination-saponification sequence to yield ±-11.
With lithium hydroxide In tetrahydrofuran; methanol; water at 20℃; for 25h; Inert atmosphere;
With water; lithium hydroxide In tetrahydrofuran; methanol at 20℃; for 25h; Inert atmosphere; 125 To a flask charged with intermediate 2.91 (786 mg, 4.11 mmol) at room temperature under N2 atmosphere was added 1 M aq. LiOH (8 mL), THF (24 mL) and MeOH (8 mL). The resulting mixture was stirred at room temperature for 25 h, then concentrated in vacuo to remove volatiles. The remaining mixture was quenched with 1 M aq. NaOH and the aqueous phase was washed with Et2O then cooled to 0 °C and acidified with 1 M aq. HCl to pH 2 and diluted with CH2Cl2. The layers were separated, and the aqueous phase was extracted with CH2Cl2 (3x). The combined organic layers were washed with brine, dried over Na2SO4, and concentrated in vacuo to afford the product, which was carried forward without additional purification.

  • 13
  • [ 3709-27-1 ]
  • [ 114527-53-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: potassium carbonate / tetrahydrofuran / 24 h / 25 °C 2: trifluoroacetic acid / dichloromethane / 1 h / 0 - 25 °C 3: bis{rhodium[3,3'-(1,3-phenylene)bis(2,2-dimethylpropanoic acid)] / 0.17 h / 0 °C
  • 14
  • [ 100-52-7 ]
  • [ 114527-53-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: 1,2-diamino-benzene; rac-Pro-OH / ethanol / 24 h / 25 °C 2: potassium carbonate / tetrahydrofuran / 24 h / 25 °C 3: trifluoroacetic acid / dichloromethane / 1 h / 0 - 25 °C 4: bis{rhodium[3,3'-(1,3-phenylene)bis(2,2-dimethylpropanoic acid)] / 0.17 h / 0 °C
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