4H-Pyrido(2,1-a)phthalazine-1-carboxamide, 10-chloro-N,N-diethyl-4-oxo-3-phenyl- → HCID 53647567, compound

HRID 477806Notes

Reaction equation

HRID 477806 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[N:7][N:8]3[C:15](=[O:16])[C:14]([C:17]4[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=4)=[CH:13][C:12]([C:23]([N:25]([CH2:28][CH3:29])[CH2:26][CH3:27])=[O:24])=[C:9]32)=[CH:4][CH:3]=1.[BH4-].[Li+]>O1CCCC1>[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][NH:7][N:8]3[C:15](=[O:16])[C:14]([C:17]4[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=4)=[CH:13][C:12]([C:23]([N:25]([CH2:28][CH3:29])[CH2:26][CH3:27])=[O:24])=[C:9]32)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 30666894H-Pyrido(2,1-a)phthalazine-1-carboxamide, 10-chloro-N,N-diethyl-4-oxo-3-phenyl-HCID 4148881Lithium borohydride2×

Product 1

HCID 53647567HCID 53647567, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2.7 g of 10-chloro-N,N-diethyl-4-oxo-3-phenyl-4H-pyrido[2,1-a]phthalazine-1-carboxamide are suspended in 65 ml of tetrahydrofuran under argon, whereupon 150 mg of lithium borohydride are added thereto, the mixture is stirred at room temperature for 4 hours, an additional 75 mg of lithium borohydride are added thereto and the mixture is stirred further until the reaction finishes. The reaction mixture is poured into 300 ml of ice-water, whereby the product crystallizes out. The crude product is chromatographed on silica gel. By recrystallization from toluene, there is obtained 10-chloro-N,N-diethyl-6,7-dihydro-4-oxo-3-phenyl-4H-pyrido[2,1-a]phthalazine-1-carboxamide of m.p. 192°-194° (toluene).

Workup

  1. additionare added
  2. stirringthe mixture is stirred further until the reaction
  3. customcrystallizes out
  4. customThe crude product is chromatographed on silica gel
  5. customBy recrystallization from toluene

Sources & evidence

ORD record
ord-b9a40d64ddf54b1d9783742b6953f9e7
Source dataset
uspto-grants-1989_12
Patent number
US04889854

Reaction notes

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