6-(2-Bromopropanoyl)-3,4-dihydroquinolin-2(1H)-one → HCID 178435112, compound

HRID 2414107Notes

Reaction equation

HRID 2414107 reaction equation
Br[CH:2]([CH3:16])[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:17]([NH:20][C:21]([NH2:23])=[S:22])(=[NH:19])[NH2:18]>C(O)C>[NH:20]([C:21]1[S:22][C:2]([CH3:16])=[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:23]=1)[C:17]([NH2:19])=[NH:18]

Participants

4

Reactant 2

HCID 130510676-(2-Bromopropanoyl)-3,4-dihydroquinolin-2(1H)-oneHCID 178513045HCID 178513045, compound

Product 1

HCID 178435112HCID 178435112, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 6-(α-bromopropionyl)-3,4-dihydrocarbostyril (7 g), amidinothiourea (3.1 g) and absolute ethanol (250 ml) is stirred under reflux overnight. The reaction mixture is cooled to ice bath temperature, and the solid filtered, washed with ethanol, dried, and suspended in aqueous sodium hydroxide. The neutralized solid is filtered, washed with water, dried and recrystallized from 50% aqueous DMF affording the desired product, M.P. >250° C.

Workup

  1. temperatureunder reflux overnight
  2. temperatureThe reaction mixture is cooled to ice bath temperature
  3. filtrationthe solid filtered
  4. washwashed with ethanol
  5. customdried
  6. filtrationThe neutralized solid is filtered
  7. washwashed with water
  8. customdried
  9. customrecrystallized from 50% aqueous DMF affording the desired product, M.P. >250° C.

Sources & evidence

ORD record
ord-3d5c18740abd4ef8a1527eebc82cdcf1
Source dataset
uspto-grants-1988_01
Patent number
US04721721

Reaction notes

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