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

HRID 641568ノート

反応式

HRID 641568 の反応式
[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]

参加物

6

反応物 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

生成物 1

HCID 574403123-Cyano-4-hydroxy-N-methylbenzamide収率 26.8%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

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]+.

後処理

  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)

出典と根拠

ORDレコード
ord-40fd796fd84642cea4096cc42659574e
出典データセット
uspto-grants-2010_04
特許番号
US07696193B2

反応ノート

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