2-Amino-6-chlorobenzoic acid → 5-chloro-2,4-dihydro-1H-3,1-benzoxazine-2,4-dione

HRID 2279788Notes

Reaction equation

HRID 2279788 reaction equation
F[C:2]1[C:11]2[C:10](=[O:12])[O:9][C:8](=[O:13])[NH:7][C:6]=2[CH:5]=[CH:4][CH:3]=1.NC1C=CC=C([Cl:24])C=1C(O)=O>>[Cl:24][C:2]1[C:11]2[C:10](=[O:12])[O:9][C:8](=[O:13])[NH:7][C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 750712-Amino-6-chlorobenzoic acidHCID 27830576-Fluoroisatoic anhydride

Product 1

HCID 6390585-chloro-2,4-dihydro-1H-3,1-benzoxazine-2,4-dione

Procedure

Prepared analogously to Compound 27E replacing 2-amino-6-fluorobenzoic acid with 2-amino-6-chlorobenzoic acid. 1H NMR (DMSO-d6, 400 MHz) δ=7.07 (dd, J=0.8, 8 Hz, 1H), 7.24-7.27 (m, 1H), 7.58-7.63 (m, 1H), 11.81 (brs, 1H).

Sources & evidence

ORD record
ord-713df35fe6d14a48a7a583509f1207b6
Source dataset
uspto-grants-2015_09
Patent number
US09133224B2

Reaction notes

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