Hydrochloric Acid → 4-(9-(1-methyl-1H-imidazol-2-yl)-3-oxo-3,7,8,9-tetrahydro-2H-pyrido[4,3,2-de]phthalazin-8-yl)benzaldehyde

HRID 907845Notes

Reaction equation

HRID 907845 reaction equation
C([O:3][CH:4](OCC)[C:5]1[CH:10]=[CH:9][C:8]([CH:11]2[NH:23][C:21]3[C:22]4[C:13](=[N:14][NH:15][C:16](=[O:24])[C:17]=4[CH:18]=[CH:19][CH:20]=3)[CH:12]2[C:25]2[N:26]([CH3:30])[CH:27]=[CH:28][N:29]=2)=[CH:7][CH:6]=1)C.Cl.C([O-])([O-])=O.[K+].[K+]>>[CH3:30][N:26]1[CH:27]=[CH:28][N:29]=[C:25]1[CH:12]1[C:13]2=[N:14][NH:15][C:16](=[O:24])[C:17]3[CH:18]=[CH:19][CH:20]=[C:21]([C:22]=32)[NH:23][CH:11]1[C:8]1[CH:9]=[CH:10][C:5]([CH:4]=[O:3])=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 1363746828-(4-(diethoxymethyl)phenyl)-9-(1-methyl-1H-imidazol-2-yl)-8,9-dihydro-2H-pyrido[4,3,2-de]phthalazin-3(7H)-one

Product 1

HCID 1363685674-(9-(1-methyl-1H-imidazol-2-yl)-3-oxo-3,7,8,9-tetrahydro-2H-pyrido[4,3,2-de]phthalazin-8-yl)benzaldehydeYield 71%

Procedure

A mixture of 8-(4-(Diethoxymethyl)phenyl)-9-(1-methyl-1H-imidazol-2-yl)-8,9-dihydro-2H-pyrido[4,3,2-de]phthalazin-3(7H)-one (50 mg, 0.11 mmol) and 2 ml of hydrochloric acid (3 N) was stirred at room temperature for 2 hr. The reaction mixture was neutralized by K2CO3 to pH=7 and then filtered, 29 mg of 4-(9-(1-methyl-1H-imidazol-2-yl)-3-oxo-3,7,8,9-tetrahydro-2H-pyrido[4,3,2-de]phthalazin-8-yl)benzaldehyde was obtained, yield 70%. LC-MS (ESI) m/z: 372 (M+1)+.

Workup

  1. filtrationfiltered

Sources & evidence

ORD record
ord-e1ac06110db24ed693eed6f70d83a5ec
Source dataset
uspto-grants-2011_09
Patent number
US08012976B2

Reaction notes

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