Hydrochloric Acid → 3-Cyano-4-hydroxy-N-methylbenzamide

HRID 641568노트

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HRID 641568 반응식
[C:1]([C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][C:12]=1[O:13]C1C=CC2CCN(C3CCC3)CCC=2C=1)[C:6]([NH:8][CH3:9])=[O:7])#[N:2].B(Br)(Br)Br.O.Cl>ClCCl>[C:1]([C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][C:12]=1[OH:13])[C:6]([NH:8][CH3:9])=[O:7])#[N:2]

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 25134Boron tribromideHCID 574403133-Cyano-4-[(3-cyclobutyl-2,3,4,5-tetrahydro-1H-3-benzazepin-7-yl)oxy]-N-methylbenzamide

생성물 1

HCID 574403123-Cyano-4-hydroxy-N-methylbenzamide수율 26.8%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

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온도
0 °C

실험 절차

3-Cyano-N-methyl-4-(methyloxy)benzamide (E279, Step 2) (346 mg, 1.82 mmol), was dissolved in dry dichloromethane (10 ml), cooled to 0° C. and treated with boron tribromide (1M solution in dichloromethane) (9.11 ml, 9.11 mmol). The mixture was stirred for 30 minutes, allowed to warm to room temperature and stirred for 18 hours. The mixture was cooled in an ice bath, treated with water added dropwise and then allowed to warm to room temperature. The mixture was poured onto 2M hydrochloric acid (10 ml) and extracted with ethyl acetate. The ethyl acetate layers were combined, dried under magnesium sulfate and evaporated in vacuo. The resulting residue was purified by column chromatography eluting with a mixture of ethyl acetate dichloromethane (1:1) to afford the title compound (86 mg); MS (ES+) m/e 177 [M+H]+.

후처리

  1. temperatureto warm to room temperature
  2. stirringstirred for 18 hours
  3. temperatureThe mixture was cooled in an ice bath
  4. additionadded dropwise
  5. temperatureto warm to room temperature
  6. extractionextracted with ethyl acetate
  7. customdried under magnesium sulfate
  8. customevaporated in vacuo
  9. customThe resulting residue was purified by column chromatography
  10. washeluting with a mixture of ethyl acetate dichloromethane (1:1)

출처 및 근거

ORD 기록
ord-40fd796fd84642cea4096cc42659574e
출처 데이터셋
uspto-grants-2010_04
특허 번호
US07696193B2

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