Methanol → Methyl 4-(aminoacetyl)phenoxyacetate hydrochloride

HRID 2419364Notes

Reaction equation

HRID 2419364 reaction equation
S(Cl)([Cl:3])=O.Cl.[NH2:6][CH2:7][C:8]([C:10]1[CH:20]=[CH:19][C:13]([O:14][CH2:15][C:16]([OH:18])=[O:17])=[CH:12][CH:11]=1)=[O:9].[CH3:21]O>>[ClH:3].[NH2:6][CH2:7][C:8]([C:10]1[CH:11]=[CH:12][C:13]([O:14][CH2:15][C:16]([O:18][CH3:21])=[O:17])=[CH:19][CH:20]=1)=[O:9]

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 145369464-(Aminoacetyl)phenoxyacetic acid hydrochloride

Product 1

HCID 20315552Methyl 4-(aminoacetyl)phenoxyacetate hydrochlorideYield 62%

Procedure

Methanol (250ml.) was stirred at -20° C. as thionyl chloride (6ml.) was added. 4-(Aminoacetyl)phenoxyacetic acid hydrochloride (5.0g) was added, and the mixture was stirred and allowed to warm to room temperature during 18 hours. The resulting solution was evaporated under reduced pressure and the residue was recrystallised from a mixture of methanol and diethyl ether to give methyl 4-(aminoacetyl)-phenoxyacetate hydrochloride, m.p. 202°-204° C. (Example 12) in 62% yield.

Workup

  1. additionwas added
  2. customThe resulting solution was evaporated under reduced pressure
  3. customthe residue was recrystallised from a mixture of methanol and diethyl ether

Sources & evidence

ORD record
ord-800387dbdf12442491dfbf59280641f7
Source dataset
uspto-grants-1978_08
Patent number
US04105790

Reaction notes

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