5-Methylcyclohexane-1,3-dione → 3-(3-Carbomethoxy-2-bromoanilino)-5-methyl-cyclohex-2-en-1-one

HRID 567224Notes

Reaction equation

HRID 567224 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].[CH3:13][CH:14]1[CH2:19][C:18](=[O:20])[CH2:17][C:16](=O)[CH2:15]1>>[C:4]([C:3]1[C:2]([Br:1])=[C:11]([CH:10]=[CH:9][CH:8]=1)[NH:12][C:16]1[CH2:15][CH:14]([CH3:13])[CH2:19][C:18](=[O:20])[CH:17]=1)([O:6][CH3:7])=[O:5]

Participants

3

Reactant 2

HCID 4580955-Methylcyclohexane-1,3-dioneHCID 13574117Methyl 3-amino-2-bromobenzoate

Product 1

HCID 227402023-(3-Carbomethoxy-2-bromoanilino)-5-methyl-cyclohex-2-en-1-oneYield 67%

Conditions

Temperature
125 °C

Procedure

A mixture of methyl 2-bromo-3-aminobenzoate (10.2 g, 44.3 mM) and 5-methyl-1,3-cyclohexanedione (6.15 g, 48.7 mm) was heated at 125° C. under a stream of nitrogen for 1.5 hours. The resultant solid was triturated with ethyl acetate to afford 9.98 g (67%) of 3-(3-carbomethoxy-2-bromoanilino)-5-methyl-cyclohex-2-en-1-one. 1H NMR (CDCl3) δ 7.55 (m, 2H), 7.35 (dd, J=8 and 8 Hz, 1H), 6.4 (bs, 1H), 5.55 (s, 1H), 3.95 (s, 3H), 2.6-2.0 (m, 5H), 1.15 (d, J=7 Hz, 3H). MS (ES) m/e 338, 340.

Workup

  1. customThe resultant solid was triturated with ethyl acetate

Sources & evidence

ORD record
ord-edb1799688444ab7a105b77a716b82c0
Source dataset
uspto-grants-2001_01
Patent number
US06177440B1

Reaction notes

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