Hydrochloric Acid → Anthranilic acid, N,N-bis(2-chloroethyl)-

Reaction equation

[Cl:1][CH2:2][CH2:3][N:4]([C:8]1[CH:18]=[CH:17][CH:16]=[CH:15][C:9]=1[C:10]([O:12]CC)=[O:11])[CH2:5][CH2:6][Cl:7].Cl>>[Cl:1][CH2:2][CH2:3][N:4]([C:8]1[CH:18]=[CH:17][CH:16]=[CH:15][C:9]=1[C:10]([OH:12])=[O:11])[CH2:5][CH2:6][Cl:7]

Participants

Reactant 2

HCID 313Hydrochloric Acid

HCID 22096864HCID 22096864, compound

Product 1

HCID 18333Anthranilic acid, N,N-bis(2-chloroethyl)-Yield 61%

Procedure

Ethyl 2-[N,N-bis(2-chloroethyl)amino]benzoate (950 mg; 3.3 mmol) was added to 15 ml of concentrated hydrochloric acid, followed by stirring for 8 hours under heating and reflux. The solvent was distilled out under reduced pressure and the residue was purified by chromatography on a silica gel column (methylene chloride→acetone), whereby 520 mg of white powder were obtained (yield: 61%).

Workup

temperatureunder heating
temperaturereflux
distillationThe solvent was distilled out under reduced pressure
customthe residue was purified by chromatography on a silica gel column (methylene chloride→acetone)

Sources & evidence

ORD record: ord-9def897171234c70a776828ed13295e9
Source dataset: uspto-grants-1998_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05852011

Reaction notes

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