Formic Acid → 2-(4-Benzyloxy-3-formylaminophenyl)ethylamine

HRID 1032537Notes

Reaction equation

HRID 1032537 reaction equation
Cl.[NH2:2][CH2:3][CH2:4][C:5]1[CH:6]=[CH:7][C:8]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[C:9]([CH:11]=1)[NH2:10].[CH:20](O)=[O:21].C(OC(=O)C)(=O)C.O>C(Cl)(Cl)Cl>[CH2:13]([O:12][C:8]1[CH:7]=[CH:6][C:5]([CH2:4][CH2:3][NH2:2])=[CH:11][C:9]=1[NH:10][CH:20]=[O:21])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

6

Reactant 4

HCID 284Formic AcidHCID 962WaterHCID 7918Acetic AnhydrideHCID 1317165715-(2-Aminoethyl)-2-benzyloxyaniline, hydrochloride

Product 1

HCID 221660012-(4-Benzyloxy-3-formylaminophenyl)ethylamine

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

2.7 g of 5-(2-aminoethyl)-2-benzyloxyaniline, hydrochloride, in 160 ml of chloroform is combined with 4 ml of a mixture of formic acid and acetic anhydride (3:5). After 5 minutes of agitation at room temperature, a small amount of water is added and the mixture completely evaporated. The residue is chromatographed on silica gel with methylene chloride/methanol 8:2. The thus-purified material is washed in methylene chloride with sodium bicarbonate solution. After evaporation, 1.5 g of 2-(4-benzyloxy-3-formylaminophenyl)ethylamine is obtained as a noncrystalline material.

Workup

  1. customthe mixture completely evaporated
  2. customThe residue is chromatographed on silica gel with methylene chloride/methanol 8:2
  3. washThe thus-purified material is washed in methylene chloride with sodium bicarbonate solution
  4. customAfter evaporation

Sources & evidence

ORD record
ord-56613acd0d0746049b163828cf4a7ec4
Source dataset
uspto-grants-1990_09
Patent number
US04958026

Reaction notes

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