Ammonia → 3-Amino-5-methylcyclohex-2-en-1-one

HRID 346046Notes

Reaction equation

HRID 346046 reaction equation
[CH3:1][CH:2]1[CH2:7][C:6](=O)[CH2:5][C:4](=[O:9])[CH2:3]1.[NH3:10]>C1C=CC=CC=1>[NH2:10][C:6]1[CH2:7][CH:2]([CH3:1])[CH2:3][C:4](=[O:9])[CH:5]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 4580955-Methylcyclohexane-1,3-dione

Product 1

HCID 30168773-Amino-5-methylcyclohex-2-en-1-one

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Conditions

Temperature
0 °C

Procedure

5-Methyl-1,3-cyclohexanedione (40 g, 0.32 mol) was dissolved in 500 ml of benzene at 70° C. The solution was heated at reflux for 2 hours, during which NH3 was bubbled through the reaction mixture and formed H2O was collected in a Dean-Stark trap. The mixture was then cooled to 0° C. and title product recovered by filtration, 39.8 g, m.p. 165°-169° C. 1H-NMR(DMSO-d6)delta(ppm): 0.98 (s, 3H), 1.6-1.88 (2H), 2.14-2.38 (2H), 3.14-3.6 (1H), 4.93 (s, 1H), 6.2-7.2 (m, 2H).

Workup

  1. temperatureThe solution was heated
  2. customwas bubbled through the reaction mixture
  3. customformed H2O
  4. customwas collected in a Dean-Stark trap
  5. filtrationtitle product recovered by filtration, 39.8 g, m.p. 165°-169° C

Sources & evidence

ORD record
ord-df3f7cfa354344999a36af4b8a6a38f8
Source dataset
uspto-grants-1991_10
Patent number
US05059609

Reaction notes

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