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

HRID 18441
Notes
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Reaction equation

HRID 18441 reaction equation
[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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 3

HCID 11
1,2-Dichloroethane
Solvent
HCID 176Acetic AcidSolvent
HCID 962WaterSolvent

Procedure

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.

Workup

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

Sources & evidence

ORD record
ord-27627b1c3a684507b64c67ddba27ff91
Source dataset
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07741352B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes