Triethylamine → 2-amino-5-bromo-N-methoxybenzamide

HRID 2279778Notes

Reaction equation

HRID 2279778 reaction equation
[NH2:1][C:2]1[CH:14]=[CH:13][C:12]([Br:15])=[CH:11][C:3]=1[C:4]([N:6](CC)CC)=[O:5].Cl.[O:17](N)[CH3:18].C(N(CC)CC)C>>[NH2:1][C:2]1[CH:14]=[CH:13][C:12]([Br:15])=[CH:11][C:3]=1[C:4]([NH:6][O:17][CH3:18])=[O:5]

Participants

4

Reactant 3

HCID 8471TriethylamineHCID 521874O-Methylhydroxylamine hydrochlorideHCID 509995132-Amino-5-bromo-N,N-diethylbenzamide

Product 1

HCID 816791802-amino-5-bromo-N-methoxybenzamideYield 65%

Procedure

Prepared analogously to Compound 3D replacing diethylamine with a mixture of methoxylamine hydrochloride (2.07 g, 24.8 mmol) and triethylamine (6.9 mL, 50 mmol) to afford 2.64 g of the title compound (65%). 1H NMR (400 MHz, CD3OD) δ=7.45 (d, J=2.3 Hz, 1H), 7.27 (dd, J=2.3, 8.8 Hz, 1H), 6.69 (d, J=8.8 Hz, 1H), 3.77 (s, 3H).

Sources & evidence

ORD record
ord-6044e20198634c8788a84e2419051720
Source dataset
uspto-grants-2015_09
Patent number
US09133224B2

Reaction notes

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