7-Amino-5,5-dimethyl-1,3,4,5-tetrahydro-benzo[b]azepin-2-one → 8-Amino-5,5-dimethyl-1,3,4,5-tetrahydro-benzo[b]azepin-2-one

HRID 1041556Notes

Reaction equation

HRID 1041556 reaction equation
NC1C=CC2NC(=O)CCC(C)(C)C=2C=1.[CH3:16][C:17]1([CH3:32])[CH2:23][CH2:22][C:21](=[O:24])[NH:20][C:19]2[CH:25]=[C:26]([N+:29]([O-])=O)[CH:27]=[CH:28][C:18]1=2>>[NH2:29][C:26]1[CH:27]=[CH:28][C:18]2[C:17]([CH3:16])([CH3:32])[CH2:23][CH2:22][C:21](=[O:24])[NH:20][C:19]=2[CH:25]=1

Participants

3

Reactant 2

HCID 578538307-Amino-5,5-dimethyl-1,3,4,5-tetrahydro-benzo[b]azepin-2-oneHCID 578538535,5-Dimethyl-8-nitro-4,5-dihydro-1H-benzo[B]azepin-2(3H)-one

Product 1

HCID 574160628-Amino-5,5-dimethyl-1,3,4,5-tetrahydro-benzo[b]azepin-2-one

Procedure

8-Amino-5,5-dimethyl-1,3,4,5-tetrahydro-benzo[b]azepin-2-one was prepared in a manner analogous to the preparation of 7-Amino-5,5-dimethyl-1,3,4,5-tetrahydro-benzo[b]azepin-2-one by using 5,5-Dimethyl-8-nitro-1,3,4,5-tetrahydro-benzo[b]azepin-2-one as starting material (98%). LCMS: m/z=205.06 (M+H+), 1H NMR (400 MHz, CDCl3) δ 7.20 (d, 1H, J=8.3 Hz), 7.11 (bs, 1H), 6.51 (m, 1H), 6.24 (m, 1H), 3.74 (bs, 2H), 2.40 (m, 2H), 2.07 (m, 2H), 1.37 (s, 6H).

Sources & evidence

ORD record
ord-74629b11689844518b62a203aa3a9dc1
Source dataset
uspto-grants-2013_10
Patent number
US08552186B2

Reaction notes

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