HCID 18620167, compound → HCID 18620145, compound

HRID 1862603Notes

Reaction equation

HRID 1862603 reaction equation
C([O:8][C:9]1[CH:17]=[CH:16][C:15]([CH2:18][CH2:19][Br:20])=[CH:14][C:10]=1[NH:11][CH:12]=[O:13])C1C=CC=CC=1>CO.[C].[Pd]>[Br:20][CH2:19][CH2:18][C:15]1[CH:16]=[CH:17][C:9]([OH:8])=[C:10]([CH:14]=1)[NH:11][CH:12]=[O:13]

Participants

4

Reactant 1

HCID 18620167HCID 18620167, compound

Product 1

HCID 18620145HCID 18620145, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

To a solution of 2′-benzyloxy-5′-(2-bromoethyl)formanilide (510 mg) in methanol (8 ml) was added 10% palladium carbon (wet, 50% water) (100 mg), and the mixture was stirred for 45 minutes at room temperature under a hydrogen atmosphere. The catalyst was filtered off, and the solvent of the filtrate was removed under reduced pressure. Purification of the residue by flash column chromatography on silica gel (eluent:methanol/dichloromethane/diethyl ether=1/10/10) gave 5′-(2-bromoethyl)-2′-hydroxyformanilide (339 mg).

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe solvent of the filtrate was removed under reduced pressure
  3. customPurification of the residue by flash column chromatography on silica gel (eluent:methanol/dichloromethane/diethyl ether=1/10/10)

Sources & evidence

ORD record
ord-14a54100c50f4ba095d3c518ca5a5a05
Source dataset
uspto-grants-2003_03
Patent number
US06538152B1

Reaction notes

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