3147-45-3|2,4-Dihydroxybenzamide| Ambeed

CAS No. :	3147-45-3
Formula :	C₇H₇NO₃
M.W :	153.14
SMILES Code :	NC(=O)C1=C(O)C=C(O)C=C1
MDL No. :	MFCD00064913
InChI Key :	IIUJCQYKTGNRHH-UHFFFAOYSA-N
Pubchem ID :	76601

Safety of [ 3147-45-3 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H315-H319
Precautionary Statements:	P264-P280-P302+P352+P332+P313+P362+P364-P305+P351+P338+P337+P313

Application In Synthesis of [ 3147-45-3 ]

* 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.

Downstream synthetic route of [ 3147-45-3 ]

[ 3147-45-3 ] Synthesis Path-Downstream 1~54

1
[ 2150-47-2 ]
[ 3147-45-3 ]

References: [1]Journal fur praktische Chemie (Leipzig 1954),1938,vol. <2> 151,p. 145,151.

2
[ 3147-45-3 ]
[ 67828-45-9 ]

References: [1]Biochemical Journal,1952,vol. 51,p. 70,76.

3
[ 3147-45-3 ]
3,5-dibromo-2,4-dihydroxy-benzoic acid amide [ No CAS ]

References: [1]Journal of the American Chemical Society,1941,vol. 63,p. 103.

4
[ 590-28-3 ]
[ 3147-45-3 ]

References: [1]Journal of the American Chemical Society,1941,vol. 63,p. 103.

5
[ 3147-45-3 ]
[ 541-41-3 ]
[ 74619-46-8 ]

Yield	Reaction Conditions	Operation in experiment
	With pyridine; In acetonitrile; at 100℃; for 2.0h;	General procedure: A solution of substituted hydroxyl substituted 4-hydroxybenzamide (5 g, 32.65 mmol) in pyridine (16.3 mL, 202.43 mmol) and acetonitrile (45 mL) was maintained at 0C during addition of ethyl chlorocarbonate (3.9 g, 35.91 mmol) in acetonitrile (15 mL) dropwise over 20 minutes. The solution so obtained was concentrated until the internal temperature reached 100 C and then refluxed for 2 h. Cooling and treating with water (100 mL) and concentrated hydrochloric acid (5 mL) yielded the compounds 1-2. They were used for the next step without further purification

References: [1]Pharmazie,1980,vol. 35,p. 49 - 50.
[2]Journal of the American Chemical Society,1957,vol. 79,p. 2811,2813.
[3]Bioorganic and Medicinal Chemistry,2016,vol. 24,p. 3472 - 3482.

6
[ 3147-45-3 ]
[ 108-24-7 ]
5-acetyl-2,4-dihydroxy-benzoic acid amide [ No CAS ]

References: [1]Journal of the Indian Chemical Society,1952,vol. 29,p. 555,558.

7
[ 3147-45-3 ]
[ 108-24-7 ]
[ 100394-37-4 ]

References: [1]Industrie Chimique Belge,1952,vol. 17,p. 478.

8
[ 3147-45-3 ]
[ 141-97-9 ]
5-hydroxy-4-methyl-2-oxo-2H-chromene-6-carboxylic acid amide [ No CAS ]

References: [1]Journal of the Indian Chemical Society,1952,vol. 29,p. 443,445.

9
[ 3147-45-3 ]
[ 141-97-9 ]
7-hydroxy-4-methyl-2-oxo-2H-chromene-6-carboxylic acid amide [ No CAS ]

References: [1]Journal of the Indian Chemical Society,1952,vol. 29,p. 443,445.

10
[ 57-13-6 ]
[ 108-46-3 ]
[ 3147-45-3 ]

References: [1]Journal of the American Chemical Society,1941,vol. 63,p. 103.

11
[ 598-50-5 ]
[ 3147-45-3 ]

References: [1]Journal of the American Chemical Society,1941,vol. 63,p. 103.

12
[ 556-89-8 ]
[ 108-46-3 ]
[ 3147-45-3 ]

References: [1]Journal of the American Chemical Society,1941,vol. 63,p. 103.

13
[ 110-91-8 ]
[ 50-00-0 ]
[ 3147-45-3 ]
[ 19045-17-1 ]

References: [1]Archiv der Pharmazie und Berichte der Deutschen Pharmazeutischen Gesellschaft,1967,vol. 300,p. 992 - 1000.

14
[ 110-91-8 ]
[ 50-00-0 ]
[ 3147-45-3 ]
[ 19045-18-2 ]

References: [1]Archiv der Pharmazie und Berichte der Deutschen Pharmazeutischen Gesellschaft,1967,vol. 300,p. 992 - 1000.

15
[ 195723-39-8 ]
[ 3147-45-3 ]
2-acetoxy-4-hydroxybenzamide [ No CAS ]

References: [1]Journal of the Indian Chemical Society,1998,vol. 75,p. 810 - 822.
[2]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1997,vol. 36,p. 507 - 512.
[3]Indian Journal of Chemistry, Section A: Inorganic, Physical, Theoretical and Analytical,1997,vol. 36,p. 507 - 512.
[4]Journal of the Indian Chemical Society,1998,vol. 75,p. 810 - 822.

16
[ 556-89-8 ]
[ 108-46-3 ]
ZnCl₂ [ No CAS ]
[ 3147-45-3 ]

References: [1]Journal of the American Chemical Society,1941,vol. 63,p. 103.

17
[ 590-28-3 ]
[ 108-46-3 ]
ZnCl₂ [ No CAS ]
[ 3147-45-3 ]

References: [1]Journal of the American Chemical Society,1941,vol. 63,p. 103.

18
[ 57-13-6 ]
[ 108-46-3 ]
ZnCl₂ [ No CAS ]
[ 3147-45-3 ]

References: [1]Journal of the American Chemical Society,1941,vol. 63,p. 103.

19
[ 598-50-5 ]
[ 108-46-3 ]
ZnCl₂ [ No CAS ]
[ 3147-45-3 ]

References: [1]Journal of the American Chemical Society,1941,vol. 63,p. 103.

Yield	Reaction Conditions	Operation in experiment
		The compounds of formula (VI) that are particularly preferred are chosen from: ... 3,5-dihydroxybenzamide 2,6-dihydroxybenzamide 2,4-dihydroxybenzamide 3-hydroxytyramine ...

22
2.4-dioxy-2'.4'-diacetoxy-benzophenone-imide [ No CAS ]
[ 3147-45-3 ]

References: [1]Journal of the Chemical Society,1924,vol. 125,p. 114.

23
[ 2969-81-5 ]
[ 3147-45-3 ]
[ 268741-81-7 ]

References: [1]Journal of Medicinal Chemistry,2000,vol. 43,p. 3815 - 3819.

24
[ 3147-45-3 ]
[ 108-94-1 ]
7-hydroxyspiro[2H-1,3-benzoxazine-2,1'-cyclohexan]-4(3H)-one [ No CAS ]

References: [1]Synthesis,2006,p. 1829 - 1835.

25
[ 89-86-1 ]
methylenediresorcylic acid [ No CAS ]
[ 3147-45-3 ]

References: [1]Journal of the Indian Chemical Society,1998,vol. 75,p. 810 - 822.

26
[ 51-01-4 ]
[ 3147-45-3 ]

References: [1]Journal of the Indian Chemical Society,1998,vol. 75,p. 810 - 822.

27
[ 50740-12-0 ]
[ 3147-45-3 ]

References: [1]Journal of the Indian Chemical Society,1998,vol. 75,p. 810 - 822.

28
[ 3147-45-3 ]
8-cyclohexylmethoxy-5-hydroxy-2,3,4,5-tetrahydro-benzo[b]oxepine-7-carboxylic acid amide [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2000,vol. 43,p. 3815 - 3819.

29
[ 3147-45-3 ]
[ 268741-84-0 ]

References: [1]Journal of Medicinal Chemistry,2000,vol. 43,p. 3815 - 3819.

30
[ 3147-45-3 ]
[ 307312-96-5 ]

References: [1]Journal of Medicinal Chemistry,2000,vol. 43,p. 3815 - 3819.

31
[ 3147-45-3 ]
[ 268741-83-9 ]

References: [1]Journal of Medicinal Chemistry,2000,vol. 43,p. 3815 - 3819.

32
[ 3147-45-3 ]
[ 307312-97-6 ]

References: [1]Journal of Medicinal Chemistry,2000,vol. 43,p. 3815 - 3819.

33
[ 3147-45-3 ]
[ 268741-82-8 ]

References: [1]Journal of Medicinal Chemistry,2000,vol. 43,p. 3815 - 3819.

34
[ 3147-45-3 ]
Phosphoric acid mono-{4-[(S)-2-acetylamino-2-((S)-7-carbamoyl-8-cyclohexylmethoxy-2,3,4,5-tetrahydro-benzo[b]oxepin-5-ylcarbamoyl)-ethyl]-phenyl} ester [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2000,vol. 43,p. 3815 - 3819.

35
[ 3147-45-3 ]
Phosphoric acid mono-{4-[(S)-2-acetylamino-2-((R)-7-carbamoyl-8-cyclohexylmethoxy-2,3,4,5-tetrahydro-benzo[b]oxepin-5-ylcarbamoyl)-ethyl]-phenyl} ester [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2000,vol. 43,p. 3815 - 3819.

36
[ 3147-45-3 ]
Phosphoric acid 4-[(S)-2-acetylamino-2-((S)-7-carbamoyl-8-cyclohexylmethoxy-2,3,4,5-tetrahydro-benzo[b]oxepin-5-ylcarbamoyl)-ethyl]-phenyl ester dibenzyl ester [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2000,vol. 43,p. 3815 - 3819.

37
[ 3147-45-3 ]
Phosphoric acid 4-[(S)-2-acetylamino-2-((R)-7-carbamoyl-8-cyclohexylmethoxy-2,3,4,5-tetrahydro-benzo[b]oxepin-5-ylcarbamoyl)-ethyl]-phenyl ester dibenzyl ester [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2000,vol. 43,p. 3815 - 3819.

38
[ 3147-45-3 ]
[ 74619-48-0 ]

References: [1]Pharmazie,1980,vol. 35,p. 49 - 50.

39
[ 3147-45-3 ]
[ 74619-47-9 ]

References: [1]Pharmazie,1980,vol. 35,p. 49 - 50.

40
[ 3147-45-3 ]
[ 19045-19-3 ]

References: [1]Archiv der Pharmazie und Berichte der Deutschen Pharmazeutischen Gesellschaft,1967,vol. 300,p. 992 - 1000.

41
[ 693286-12-3 ]
[ 3147-45-3 ]
[ 693276-66-3 ]

Yield	Reaction Conditions	Operation in experiment
	With copper; potassium carbonate; In 1-methyl-pyrrolidin-2-one; at 150℃;Heating / reflux;	A mixture of 4- [4-CHLORO-6- (2, 6-DIETHYL-PHENYL)-2-METHYL-PYRIDIN-3-YLMETHYL]-2, 2- dimethyl-morpholine (30 mg, 0. 08 mmol), 2, 4-DIHYDROXY-BENZAMIDE (24 mg, 0. 16 MMOL), copper powder (10 mg) and K2C03 (22 mg, 0.16 mmol) in 1-METHYL-2-PYRROLIDINONE (1 mL) is heated at 150 C OVERNIGHT. After cooling, EtOAc (10 mL) and water (10 mL) are added to the mixture. The organic layer is separated, washed with brine (3*), dried (NA2SO4) and concentrated. The crude is purified by PTLC (1: 1 Hexane/EtOAc) to give to give the title COMPOUND.'H NMR (CDC13) 12.41 (s, 1H), 7.35 (d, 2H), 7.23 (M, 1H), 7.10 (M, 2H), 6.63 (s, 1H), 6.51 (M, 2H), 5.85 (br, 2H), 3.72 (M, 2H), 3.56 (s, 2H), 2.74 (s, 3H), 2.41-2. 30 (M, 6H), 1.20 (s, 6H), 1.76 (M, 2H), 1.01 (t, 6H).

References: [1]Patent: WO2004/43925,2004,A2 .Location in patent: Page 112; 181.

42
[ 3147-45-3 ]
[ 74454-59-4 ]

Yield	Reaction Conditions	Operation in experiment
		(a) 2,3-Dihydro-2,2-dimethyl-7-hydroxy-4H-1,3-benzoxazin-4-one with a melting point of 249-251 is obtained analogously to Example 1(a) from <strong>[3147-45-3]2,4-dihydroxybenzamide</strong>.
		(2a) Analogously to Example (1a), from <strong>[3147-45-3]2,4-dihydroxybenzamide</strong> there is obtained 2,3-dihydro-2,2-dimethyl-7-hydroxy-4H-1,3-benzoxazin-4-one having a melting point of 249-251.
		(43a) According to the method described by Irvine et al., Synthesis 1972, 568, <strong>[3147-45-3]2,4-dihydroxybenzamide</strong> is converted, using an excess of acetone, into 2,3-dihydro-2,2-dimethyl-7-hydroxy-4H-1,3-benzoxazin-4-one, m.p. 249-251.

References: [1]Patent: US4460580,1984,A .
[2]Patent: US4497813,1985,A .
[3]Patent: US4497813,1985,A .

43
[ 3147-45-3 ]
[ 6046-93-1 ]
{Cu(C₇H₆NO₃)2} [ No CAS ]

References: [1]Journal fur praktische Chemie (Leipzig 1954),1938,vol. 151,p. 145 - 159.

44
[ 13874-09-4 ]
[ 3147-45-3 ]
{Cu(C₇H₆NO₃)2} [ No CAS ]

References: [1]Journal fur praktische Chemie (Leipzig 1954),1938,vol. 151,p. 145 - 159.

45
[ 95-01-2 ]
[ 3147-45-3 ]

References: [1]European Journal of Organic Chemistry,2011,p. 2226 - 2229.

46
[ 33617-59-3 ]
[ 3147-45-3 ]

References: [1]Catalysis Communications,2012,vol. 26,p. 48 - 53.

47
[ 3147-45-3 ]
dimethylcarbamic acid-3-[2-fluoro-3-(N-benzylsulfamoylamino)benzyl]-2,4-dioxo-3,4-dihydro-1,3-benzoxazine-7-yl ester [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry,2016,vol. 24,p. 3472 - 3482.

48
[ 3147-45-3 ]
7-(N,N-dimethylcarbamoyloxy)-1,3-benzoxazine-2,4(3H)-dione [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry,2016,vol. 24,p. 3472 - 3482.

49
[ 3147-45-3 ]
dimethylcarbamic acid 3-(2-nitrobenzyl)-2,4-dioxo-3,4-dihydro-1,3-benzoxazine-7-yl ester [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry,2016,vol. 24,p. 3472 - 3482.

50
[ 3147-45-3 ]
dimethylcarbamic acid 3-(4-nitrobenzyl)-2,4-dioxo-3,4-dihydro-1,3-benzoxazine-7-yl ester [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry,2016,vol. 24,p. 3472 - 3482.

51
[ 3147-45-3 ]
dimethylcarbamic acid 3-(2-fluoro-3-nitrobenzyl)-2,4-dioxo-3,4-dihydro-1,3-benzoxazine-7-yl ester [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry,2016,vol. 24,p. 3472 - 3482.

52
[ 3147-45-3 ]
dimethylcarbamic acid 3-(4-fluoro-3-nitrobenzyl)-2, 4-dioxo-3,4-dihydro-1,3-benzoxazine-7-yl ester [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry,2016,vol. 24,p. 3472 - 3482.

53
[ 3147-45-3 ]
7-(N,N-dimethylcarbamoyloxy)-3-(2-fluoro-3-aminobenzyl)-1,3-benzoxazine-2,4(3H)-dione [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry,2016,vol. 24,p. 3472 - 3482.

54
[ 3147-45-3 ]
dimethylcarbamic acid-3-[2-fluoro-3-(methylsulfonamido)benzyl]-2,4-dioxo-3,4-dihydro-1,3-benzoxazine-7-yl ester [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry,2016,vol. 24,p. 3472 - 3482.

Historical Records

Technical Information

• Acidity of Phenols • Acyl Group Substitution • Alkyl Halide Occurrence • Buchwald-Hartwig C-N Bond and C-O Bond Formation Reactions • Chan-Lam Coupling Reaction • Complex Metal Hydride Reductions • Electrophilic Substitution of the Phenol Aromatic Ring • Etherification Reaction of Phenolic Hydroxyl Group • Halogenation of Phenols • Hydride Reductions • Lawesson's Reagent • Leuckart-Wallach Reaction • Mannich Reaction • Oxidation of Phenols • Pechmann Coumarin Synthesis • Petasis Reaction • Preparation of Aldehydes and Ketones • Preparation of Amines • Reactions of Amines • Reactions of Benzene and Substituted Benzenes • Reimer-Tiemann Reaction • Specialized Acylation Reagents-Carbodiimides and Related Reagents • Specialized Acylation Reagents-Ketenes • Specialized Acylation Reagents-Vilsmeier Reagent • Ugi Reaction

Related Functional Groups of
[ 3147-45-3 ]

Aryls

A683707 [3147-50-0]

2,6-Dihydroxybenzamide

Similarity: 1.00

A140736 [39506-61-1]

2-Hydroxy-5-methylbenzamide

Similarity: 0.97

A697018 [14008-60-7]

2-Hydroxy-3-methylbenzamide

Similarity: 0.97

A364818 [65-45-2]

2-Hydroxybenzamide

Similarity: 0.97

Amides

A683707 [3147-50-0]

2,6-Dihydroxybenzamide

Similarity: 1.00

A140736 [39506-61-1]

2-Hydroxy-5-methylbenzamide

Similarity: 0.97

A697018 [14008-60-7]

2-Hydroxy-3-methylbenzamide

Similarity: 0.97

A364818 [65-45-2]

2-Hydroxybenzamide

Similarity: 0.97

Amines

A683707 [3147-50-0]

2,6-Dihydroxybenzamide

Similarity: 1.00

A140736 [39506-61-1]

2-Hydroxy-5-methylbenzamide

Similarity: 0.97

A697018 [14008-60-7]

2-Hydroxy-3-methylbenzamide

Similarity: 0.97

A364818 [65-45-2]

2-Hydroxybenzamide

Similarity: 0.97

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P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
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H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

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CAS No.: 3147-45-3

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