Triethylamine → Benzoyl chloride, 2-chloro-5-nitro-

HRID 1399422Notes

Reaction equation

HRID 1399422 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].S(Cl)([Cl:16])=[O:15].[CH2:18]([N:20](CC)CC)[CH3:19]>>[Cl:1][C:2]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][C:3]=1[C:4]([Cl:16])=[O:5].[NH2:20][CH2:18][C:19]([O:6][CH2:4][C:3]1[CH:2]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:15]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 172872-Chloro-5-nitrobenzoic acidHCID 24386Thionyl Chloride

Product 2

HCID 117637Benzoyl chloride, 2-chloro-5-nitro-HCID 409140Benzyl glycinate

Procedure

As shown in scheme E, reaction of 2-chloro-5-nitrobenzoic acid with thionyl chloride gave 2-chloro-5-nitrobenzoyl chloride, which on further treatment with benzyl glycinate in the presence of triethylamine gave benzyl 2-(2-chloro-5-nitrobenzamido)acetate (intermediate 6). Treatment of intermediate 6 either with K18F or K19F in the presence of kryptofix [2.2.2] or 18-crown-6 to yield benzyl 2-(2-fluoro-5-nitrobenzamido)acetate, which on further reduction with hydrogen gas or hydrogen source in the presence of Pd/C gave 2-(5-amino-2-fluorobenzamido)acetic acid (compound 5).

Sources & evidence

ORD record
ord-bb2b5d132f7f442d9ff538c646a6f24f
Source dataset
uspto-grants-2014_12
Patent number
US08906344B2

Reaction notes

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