4-Nitroanthranilic acid → 2-Amino-4-nitrobenzoyl chloride

HRID 889437Notes

Reaction equation

[NH2:1][C:2]1[CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[CH:8]=[CH:7][C:3]=1[C:4](O)=[O:5].S(Cl)([Cl:16])=O>>[NH2:1][C:2]1[CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[CH:8]=[CH:7][C:3]=1[C:4]([Cl:16])=[O:5]

Participants

Reactant 2

HCID 120764-Nitroanthranilic acid

HCID 24386Thionyl Chloride

Product 1

HCID 214891672-Amino-4-nitrobenzoyl chlorideYield 119.8%

Procedure

2-Amino-4-nitrobenzoic acid (15 g, 82 mmol) was refluxed with sulfurous dichloride (40 mL, 82 mmol) for 2.5 hours. The reaction mixture was cooled to room temperature and concentrated to give Intermediate 69A (19.7 g, 119%) as a brown oil. HPLC: Rt=2.323 (as methyl ester) min. (CHROMOLITH® column 4.6×50 mm eluting with 10-90% aqueous methanol over 4 min. containing 0.1% TFA, 4 mL/min., monitoring at 220 nm.). MS (ES): m/z=197 (as methyl ester) [M+H]+.

Workup

concentrationconcentrated

Sources & evidence

ORD record: ord-af787e895f6b4bf089469efea35f5a1b
Source dataset: uspto-grants-2012_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08252795B2

Reaction notes

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