Sodium borohydride → HCID 20377591, compound

HRID 2052282Notes

Reaction equation

HRID 2052282 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]1[CH:12]=[CH:13][N:14]=[C:7]1[N:6]=[C:5]2[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[BH4-].[Na+]>C(O)C>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]1[CH:12]=[CH:13][N:14]=[C:7]1[NH:6][CH:5]2[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]1[CH2:12][CH2:13][N:14]=[C:7]1[NH:6][CH:5]2[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 20377597HCID 20377597, compound

Product 2

HCID 20377591HCID 20377591, compoundHCID 135737536HCID 135737536, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a suspension of 0.28 g of 7-chloro-5-phenylimidazo[1,2-a]quinazoline in 20 ml of ethanol was added 0.2 g of sodium borohydride, and the mixture was heated under reflux for 10 hours. After cooling, the mixture was poured into ice-water, and the resulting precipitate was collected by filtration, washed with water and dried. The product was dissolved in chloroform and absorbed on an activated alumina column. Elution with chloroform and recrystallization from ethanol gave 7-chloro-4,5-dihydro-5-phenylimidazo[1,2-a]quinazoline (m.p. 239°-241° C.) and 7-chloro-1,2,4,5-tetrahydro-5-phenylimidazo[1,2-a]quinazoline (m.p. 210°-213° C.).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 10 hours
  3. temperatureAfter cooling
  4. filtrationthe resulting precipitate was collected by filtration
  5. washwashed with water
  6. customdried
  7. dissolutionThe product was dissolved in chloroform
  8. customabsorbed on an activated alumina column
  9. washElution
  10. customwith chloroform and recrystallization from ethanol

Sources & evidence

ORD record
ord-af6f4344069f4949a76e8ae918c6d899
Source dataset
uspto-grants-1980_01
Patent number
US04183932

Reaction notes

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