6-Fluoroisatoic anhydride → 6-amino-3-bromo-2-methyl-N-methylbenzamide

HRID 2279792Notes

Reaction equation

HRID 2279792 reaction equation
[NH2:1][C:2]1[C:7]([C:8]([NH:10][CH3:11])=[O:9])=[C:6](F)[C:5]([Br:13])=[CH:4][CH:3]=1.F[C:15]1C2C(=O)OC(=O)NC=2C=CC=1.CC1C2C(=O)OC(=O)NC=2C=CC=1>>[NH2:1][C:2]1[C:7]([C:8]([NH:10][CH3:11])=[O:9])=[C:6]([CH3:15])[C:5]([Br:13])=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 27830576-Fluoroisatoic anhydrideHCID 104875225-methyl-2,4-dihydro-1H-3,1-benzoxazine-2,4-dione2×HCID 866977326-amino-3-bromo-2-fluoro-N-methylbenzamide

Product 1

HCID 866977396-amino-3-bromo-2-methyl-N-methylbenzamide

Procedure

Prepared analogously to Compound 27D replacing 5-fluoro-1H-benzo[d][1,3]oxazine-2,4-dione (Compound 27E) with 5-methyl-1H-benzo[d][1,3]oxazine-2,4-dione (Compound 29E). 1H NMR (CDCl3, 500 MHz) δ 2.32 (s, 3H), 2.98 (d, J=4.8 Hz, 3H), 4.0 (br.s, 2H), 5.81 (br.s, 1H), 6.42 (d, J=8.8 Hz, 1H), 7.27 (d, J=8.8 Hz, 1H).

Sources & evidence

ORD record
ord-fa3f372511e04ac7807fab5d79d50367
Source dataset
uspto-grants-2015_09
Patent number
US09133224B2

Reaction notes

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