Triethylamine → Methyl 4-(3-hydroxyanilino)-4-oxobutanoate

HRID 465133

Reaction equation

HRID 465133 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1.C(N(CC)CC)C.[C:16]([CH2:20][CH2:21][C:22](Cl)=[O:23])([O:18][CH3:19])=[O:17]>O1CCCC1>[OH:8][C:4]1[CH:3]=[C:2]([NH:1][C:22](=[O:23])[CH2:21][CH2:20][C:16]([O:18][CH3:19])=[O:17])[CH:7]=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 115683-AminophenolHCID 73888Butanoic acid, 4-chloro-4-oxo-, methyl ester

Product 1

HCID 13491817Methyl 4-(3-hydroxyanilino)-4-oxobutanoateYield 88%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To an ice cold solution of 3-aminophenol (21.8 g, 0.2 mol) and triethylamine (21.3 g, 0.2 mol) in tetrahydrofuran (250 ml) is added a solution of 3-carbomethoxypropanoyl chloride (30.1 g, 0.2 mol) in tetrahydrofuran. The reaction is allowed to warm to room temperature and is filtered through a pad of Celite and silica gel. The solvent is removed in vacuo to give a solid. Recrystallization from ethyl acetate gives 39.3 g (88% yield) of product, m.p. 144.5°-146° C.

Workup

  1. filtrationis filtered through a pad of Celite and silica gel
  2. customThe solvent is removed in vacuo
  3. customto give a solid
  4. customRecrystallization from ethyl acetate

Sources & evidence

ORD record
ord-5584d776a8db4dcc8b6c5a6e6f45bfb2
Source dataset
uspto-grants-1985_10
Patent number
US04550172

Linked notes

Loading…