Cyclohexanone → HCID 178429192, compound

HRID 1076830Notes

Reaction equation

HRID 1076830 reaction equation
[C:1]1(=O)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C([O:10][C:11](=O)[CH2:12][C:13]([CH3:15])=O)C.C([O-])(=O)C.[NH4+:21]>O>[OH:10][C:11]1[CH:12]=[C:13]([CH3:15])[C:1]2[CH2:6][CH2:5][CH2:4][CH2:3][C:2]=2[N:21]=1

Participants

5

Reactant 3

HCID 7967CyclohexanoneHCID 8868Ethyl AcetoacetateHCID 517165Ammonium Acetate

Product 1

HCID 178429192HCID 178429192, compoundYield 5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

98.15 G. (1.0 mole) of cyclohexanone, 130 g. (1.0 mole) of ethylacetoacetate and 77.1 g. (1.0 mole) of ammonium acetate are heated at reflux for 14 hours. The reaction mixture is cooled in ice and diluted with water. The resultant precipitate is collected by filtration, washed with ether and dried in air affording 8.0 g (5%) of 2-hydroxy-4-methyl-5,6,7,8-tetrahydroquinoline, m.p. 250°-252°C.

Workup

  1. temperatureat reflux for 14 hours
  2. temperatureThe reaction mixture is cooled in ice
  3. filtrationThe resultant precipitate is collected by filtration
  4. washwashed with ether
  5. customdried in air

Sources & evidence

ORD record
ord-54e9386f7c714e03a12523ac335c1f0b
Source dataset
uspto-grants-1976_05
Patent number
US03957997

Reaction notes

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