Diisobutylaluminumhydride → Pirquinozol

HRID 1448162Notes

Reaction equation

HRID 1448162 reaction equation
C([O:3][C:4]([C:6]1[CH:18]=[C:17]2[N:8]([C:9](=[O:19])[NH:10][C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][C:16]=32)[N:7]=1)=O)C.[H-].C([Al+]CC(C)C)C(C)C>ClCCl>[OH:3][CH2:4][C:6]1[CH:18]=[C:17]2[N:8]([C:9](=[O:19])[NH:10][C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][C:16]=32)[N:7]=1

Participants

4

Reactant 2

HCID 21225700Diisobutylaluminumhydride2×HCID 1360233445,6-Dihydro-5-oxopyrazolo[1,5-c]quinazoline-2-carboxylic acid ethyl ester

Product 1

HCID 135449340Pirquinozol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1.28 g (0.005 mole) of 5,6-dihydro-5-oxopyrazolo-[1,5-c]quinazoline-2-carboxylic acid ethyl ester prepared as described in Example 2A is suspended in 100 ml of dichloromethane and treated with 7.9 ml (0.011 mole) of 20% di-isobutylaluminum hydride (Dibal). The resultant yellow solution is stirred at room temperature for 45 minutes, 2.0 ml (0.003 M) of Dibal solution is added and stirring continued for 17 hours.

Workup

  1. stirringstirring
  2. waitcontinued for 17 hours

Sources & evidence

ORD record
ord-1cb241515dc94ceb99a926b5d9e077a0
Source dataset
uspto-grants-1979_12
Patent number
US04179561

Reaction notes

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