Water → Methyl 3-amino-5-(hydroxymethyl)benzoate

HRID 49313

반응식

HRID 49313 반응식
[N+:1]([C:4]1[CH:5]=[C:6]([CH:10]=[C:11]([C:13]([O:15][CH3:16])=[O:14])[CH:12]=1)[C:7](O)=[O:8])([O-])=O.O.C(=O)([O-])[O-].[K+].[K+]>C1COCC1>[NH2:1][C:4]1[CH:12]=[C:11]([CH:10]=[C:6]([CH2:7][OH:8])[CH:5]=1)[C:13]([O:15][CH3:16])=[O:14]

참가 물질

5

반응물 3

HCID 962WaterHCID 11430Potassium CarbonateHCID 747761,3-Benzenedicarboxylic acid, 5-nitro-, 1-methyl ester

생성물 1

HCID 10535399Methyl 3-amino-5-(hydroxymethyl)benzoate수율 93.6%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

85 g of 3-nitro-5-methoxycarbonylbenzoic acid was dissolved in 200 ml of THF under a flow of nitrogen, and 43.4 ml of borane dimethylsulfide complex was added with stirring under ice-cooling. After stirring for 18 hours, 200 ml of water was added, and then 96 g of potassium carbonate was added. It was extracted with ethyl acetate, and theorganic layer was washed with salt solution. After drying with magnesium sulfate, the resulting solid was dissolved in 800 ml of ethyl acetate, 750 mg of 10% Pd/C was added, and stirring was continued under the flow of hydrogen. After the reaction was completed, it was subjected to the filtration, and then the filtrate was concentrated to produce 64 g of the title compound.

후처리

  1. additionwas added
  2. temperaturecooling
  3. stirringAfter stirring for 18 hours
  4. extractionIt was extracted with ethyl acetate, and theorganic layer
  5. washwas washed with salt solution
  6. dry with materialAfter drying with magnesium sulfate
  7. dissolutionthe resulting solid was dissolved in 800 ml of ethyl acetate
  8. addition750 mg of 10% Pd/C was added
  9. stirringstirring
  10. filtrationit was subjected to the filtration
  11. concentrationthe filtrate was concentrated

출처 및 근거

ORD 기록
ord-39ab0bf8396c4e4589cc7a8137c09994
출처 데이터셋
uspto-grants-2004_03
특허 번호
US06706745B1

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