4-Bromobenzaldehyde → 4-(4-Bromo-benzylamino)-2-hydroxy-benzoic acid methyl ester

HRID 18441

반응식

HRID 18441 반응식
[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7]([NH2:10])=[CH:6][C:5]=1[OH:11].[Br:13][C:14]1[CH:21]=[CH:20][C:17]([CH:18]=O)=[CH:16][CH:15]=1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].C([O-])(O)=O.[Na+]>CC(O)=O.ClCCCl.O>[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7]([NH:10][CH2:18][C:17]2[CH:20]=[CH:21][C:14]([Br:13])=[CH:15][CH:16]=2)=[CH:6][C:5]=1[OH:11]

참가 물질

8

반응물 4

HCID 707414-BromobenzaldehydeHCID 77787Methyl p-aminosalicylateHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydride

생성물 1

HCID 586858634-(4-Bromo-benzylamino)-2-hydroxy-benzoic acid methyl ester수율 58%

시약·촉매·용매 3

HCID 111,2-Dichloroethane용매HCID 176Acetic Acid용매HCID 962Water용매

실험 절차

To a solution of 4-amino-2-hydroxy benzoic acid methyl ester (836 mg; 5 mmol) and 4-bromobenzaldehyde (926 mg; 5 mmol) in 1 M HOAc in 1,2-dichloroethane (5 mL) was added at once NaBH(OAc)3 (1.49 g; 7 mmol) and the reaction mixture was stirred at room temperature overnight. Water (25 mL) was added and the inhomogeneous mixture was neutralized using solid NaHCO3. The organic layer was isolated, dried, evaporated to dryness and recrystallised from isopropyl ether/dichloromethane/heptane to yield 970 mg (58%) of a yellow solid. NMR and GC-MS in accordance with structure.

후처리

  1. customThe organic layer was isolated
  2. customdried
  3. customevaporated to dryness
  4. customrecrystallised from isopropyl ether/dichloromethane/heptane

출처 및 근거

ORD 기록
ord-27627b1c3a684507b64c67ddba27ff91
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07741352B2

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