Ammonia → 7-Amino-4,4-dimethyl-3,4-dihydroquinolin-2(1H)-one

HRID 1492165Notes

Reaction equation

HRID 1492165 reaction equation
C([NH:4][C:5]1[CH:14]=[C:13]2[C:8]([C:9]([CH3:17])([CH3:16])[CH2:10][C:11](=[O:15])[NH:12]2)=[CH:7][CH:6]=1)(=O)C.Cl.N>C(O)C>[NH2:4][C:5]1[CH:14]=[C:13]2[C:8]([C:9]([CH3:17])([CH3:16])[CH2:10][C:11](=[O:15])[NH:12]2)=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 14476477N-(4,4-dimethyl-2-oxo-1,2,3,4-tetrahydroquinolin-7-yl)acetamide

Product 1

HCID 144764787-Amino-4,4-dimethyl-3,4-dihydroquinolin-2(1H)-one

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A suspension of 23.2 g. (0.1 mole) 7-acetamido-1,2,3,4-tetrahydro-4,4-dimethylquinolin-2-one, 200 ml. ethanol and 20 ml. concentrated hydrochloric acid is boiled under reflux until dissolving is complete. pH value is then adjusted with ammonia to 8, the reaction mixture is extracted three times with dichloromethane and the organic phase is dried over anhydrous sodium sulphate and freed from solvent. Yield 13.1 g. (69% of theory); m.p. 161°-163° C.

Workup

  1. additionA suspension of 23.2 g
  2. temperatureunder reflux
  3. dissolutionuntil dissolving
  4. extractionthe reaction mixture is extracted three times with dichloromethane
  5. dry with materialthe organic phase is dried over anhydrous sodium sulphate

Sources & evidence

ORD record
ord-6c89475eaf6c4b409c74676d55c0a454
Source dataset
uspto-grants-1994_12
Patent number
US05373019

Reaction notes

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