Hydrochloric Acid → Methyl 4-(aminoacetyl)phenoxyacetate hydrochloride

HRID 2419381Notes

Reaction equation

[N:1]([CH2:4][C:5]([C:7]1[CH:18]=[CH:17][C:10]([O:11][CH2:12][C:13]([O:15][CH3:16])=[O:14])=[CH:9][CH:8]=1)=[O:6])=[N+]=[N-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[ClH:38].CCOCC>O1CCCC1>[ClH:38].[NH2:1][CH2:4][C:5]([C:7]1[CH:8]=[CH:9][C:10]([O:11][CH2:12][C:13]([O:15][CH3:16])=[O:14])=[CH:17][CH:18]=1)=[O:6]

Participants

Conditions

Temperature: 40 °C

Procedure

Methyl 4-(azidoacetyl)phenoxyacetate (2.49g.) was added to a stirred solution of triphenylphosphine (2.62g.) in tetrahydrofuran (20ml.) maintained at 40° C. The solution gradually became orange during the addition of the azido compound and was further stirred at 40° C. for 15 minutes after the addition was complete. 1N-Hydrochloric acid (20ml.) was then added and the mixture stirred at 40° C. for 15 minutes. The mixture was cooled to room temperature and then ether (200ml.) was added. The ethereal layer was decanted off and the brown oily residue was dissolved in toluene (20ml.) and the solution obtained was evaporated in vacuo. The solid residue formed was then recrystallised twice from methanol to give methyl 4-(aminoacetyl)phenoxyacetate hydrochloride (0.7g.), m.p. 202°-204° C.

Workup

additionafter the addition
stirringthe mixture stirred at 40° C. for 15 minutes
temperatureThe mixture was cooled to room temperature
customThe ethereal layer was decanted off
dissolutionthe brown oily residue was dissolved in toluene (20ml.)
customthe solution obtained
customwas evaporated in vacuo
customThe solid residue formed
customwas then recrystallised twice from methanol

Sources & evidence

ORD record: ord-3604bc81c75d4d32b3530adfc8532c45
Source dataset: uspto-grants-1978_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04105790

Reaction notes

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