1,3-Cyclohexanedione → 3-(3-Carbomethoxy-2-bromoanilino)cyclohex-2-en-1-one

HRID 585593Notes

Reaction equation

HRID 585593 reaction equation
[Br:1][C:2]1[C:11]([NH2:12])=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[C:13]1(=O)[CH2:18][CH2:17][CH2:16][C:15](=[O:19])[CH2:14]1>>[C:4]([C:3]1[C:2]([Br:1])=[C:11]([CH:10]=[CH:9][CH:8]=1)[NH:12][C:13]1[CH2:18][CH2:17][CH2:16][C:15](=[O:19])[CH:14]=1)([O:6][CH3:7])=[O:5]

Participants

3

Reactant 2

HCID 104341,3-CyclohexanedioneHCID 13574117Methyl 3-amino-2-bromobenzoate

Product 1

HCID 223377243-(3-Carbomethoxy-2-bromoanilino)cyclohex-2-en-1-oneYield 92.5%

Conditions

Temperature
125 °C

Procedure

A mixture of methyl 2-bromo-3-aminobenzoate (13.2 g, 60.0 mM) and 1,3-cyclohexanedione (8.4 g, 75 mM) was heated at 125° C. under a stream of nitrogen for 4 hours. The resultant solid was purified by HPLC on silica gel (elution with methylene chloride/ethyl acetate) to afford 17.2 g (88%) of 3-(3-carbomethoxy-2-bromoanilino)cyclohex-2-en-1-one as a tan foam. 1H NMR (DMSO-d6) δ 8.75 (s, 1H), 7.6-7.4 (m, 3H), 4.65 (s, 1H), 3.85 (s, 3H), 2.6 (t, 2H, J=6 Hz), 2.15 (t, 2H, J=6 Hz), and 1.9 (m, 2H). IR (CHCl3, cm−1) 3400, 3004, 2954, 1732, 1607, 1588, 1573, 1513, 1464, 1436, 1412, 1308, 1249, 1177, and 1144. MS (ES) m/e 322, 324, 326.

Workup

  1. customThe resultant solid was purified by HPLC on silica gel (elution with methylene chloride/ethyl acetate)

Sources & evidence

ORD record
ord-8ec771ac31db4d389b0ed147bf7e7a9e
Source dataset
uspto-grants-2005_08
Patent number
US06933313B2

Reaction notes

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