6-(2-Chloroacetyl)-1,2,3,4-tetrahydroquinolin-2-one → HCID 178512604, compound

HRID 2414105Notes

Reaction equation

HRID 2414105 reaction equation
Cl[CH2:2][C:3]([C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[NH:11][C:10](=[O:15])[CH2:9][CH2:8]2)=O.[C:16]([NH:19][C:20]([NH2:22])=[S:21])(=[NH:18])[NH2:17]>C(O)C>[NH:19]([C:20]1[S:21][CH:2]=[C:3]([C:5]2[CH:6]=[C:7]3[C:12](=[CH:13][CH:14]=2)[NH:11][C:10](=[O:15])[CH2:9][CH2:8]3)[N:22]=1)[C:16]([NH2:18])=[NH:17]

Participants

4

Reactant 2

HCID 49617906-(2-Chloroacetyl)-1,2,3,4-tetrahydroquinolin-2-oneHCID 178513045HCID 178513045, compound

Product 1

HCID 178512604HCID 178512604, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 6-(chloroacetyl)-3,4-dihydrocarbostyril (7 g), amidinothiourea (3.8 g) and absolute ethanol (250 ml) is stirred under reflux for about 24 hours. The reaction mixture is cooled to ice bath temperature and the precipitate filtered, washed with ethanol, and dried. The solid is suspended in aqueous sodium hydroxide, filtered, the filtered solid washed with water, and dried in vacuo. The dried solid is recrystallized from 50% aqueous DMF, and dried in vacuo yielding the desired product, M.P. >250° C.

Workup

  1. temperatureunder reflux for about 24 hours
  2. temperatureThe reaction mixture is cooled to ice bath temperature
  3. filtrationthe precipitate filtered
  4. washwashed with ethanol
  5. customdried
  6. filtrationfiltered
  7. washthe filtered solid washed with water
  8. customdried in vacuo
  9. customThe dried solid is recrystallized from 50% aqueous DMF
  10. customdried in vacuo

Sources & evidence

ORD record
ord-36234ec5af314deeaa38db29bd0aa876
Source dataset
uspto-grants-1988_01
Patent number
US04721721

Reaction notes

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