Formic Acid → HCID 22166007, compound

HRID 1032535Notes

Reaction equation

HRID 1032535 reaction equation
[CH:1]([OH:3])=O.[C:4]([O:7][C:8](=O)[CH3:9])(=O)[CH3:5].C(O[NH:19][C:20]1[CH:25]=[C:24]([CH2:26][CH2:27][N:28]([CH2:32][CH2:33][CH3:34])[CH2:29][CH2:30][CH3:31])[CH:23]=CC=1)C1C=CC=CC=1>C(Cl)(Cl)Cl>[CH2:4]([O:7][C:8]1[CH:9]=[CH:23][C:24]([CH2:26][CH2:27][N:28]([CH2:29][CH2:30][CH3:31])[CH2:32][CH2:33][CH3:34])=[CH:25][C:20]=1[NH:19][CH:1]=[O:3])[C:5]1[CH:27]=[CH:26][CH:24]=[CH:25][CH:20]=1

Participants

5

Reactant 3

HCID 284Formic AcidHCID 7918Acetic AnhydrideHCID 86744226HCID 86744226, compound

Product 1

HCID 22166007HCID 22166007, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Under ice cooling, 4 ml of a mixture of formic acid and acetic anhydride (ratio 3:5) is added dropwise to 3.2 g of 2-(benzyloxy-5-(2-dipropylaminoethyl)aniline in 10 ml of chloroform, then the mixture is stirred for 2 hours at room temperature. The solution is washed with aqueous NaHCO3 solution, concentrated, and the residue chromatographed on silica gel with methylene chloride/acetone (1:1), yielding 1.8 g of N-[2-benzyloxy-5-(2-dipropylaminoethyl)phenyl]formamide as an oil.

Workup

  1. washThe solution is washed with aqueous NaHCO3 solution
  2. concentrationconcentrated
  3. customthe residue chromatographed on silica gel with methylene chloride/acetone (1:1)

Sources & evidence

ORD record
ord-4eb7c9c5f64b4f9c966cbe03d05beb7a
Source dataset
uspto-grants-1990_09
Patent number
US04958026

Reaction notes

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