Ethylamine → 2-Amino-5-bromo-N-ethylbenzamide

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)[CH2:7][CH3:8])=[O:5].C(N)C>>[NH2:1][C:2]1[CH:14]=[CH:13][C:12]([Br:15])=[CH:11][C:3]=1[C:4]([NH:6][CH2:7][CH3:8])=[O:5]

Participants

Reactant 2

HCID 6341Ethylamine

HCID 509995132-Amino-5-bromo-N,N-diethylbenzamide

Product 1

HCID 187118562-Amino-5-bromo-N-ethylbenzamideYield 70%

Procedure

Prepared analogously to Compound 3D replacing diethylamine with ethylamine to afford 1.41 g of the title product (70%). 1H NMR (400 MHz, CD3OD) δ 7.55 (d, J=2.3 Hz, 1H), 7.25 (dd, J=2.4, 8.7 Hz, 1H), 6.67 (d, J=8.8 Hz, 1H), 3.32-3.38 (m, 2H), 1.20 (t, J=7.3 Hz, 3H). MS (ESI): m/z 243.33 [M+H]+. UPLC: tR=0.98 min (UPLC-SQD: analytical—2 min).

Sources & evidence

ORD record: ord-ee61a3792c1e4a2ba089437064b13829
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09133224B2

Reaction notes

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