8-(4-(Dimethoxymethyl)phenyl)-9-phenyl-8,9-dihydro-2H-pyrido[4,3,2-de]phthalazin-3(7H)-one → 4-(3-Oxo-9-phenyl-3,7,8,9-tetrahydro-2H-pyrido[4,3,2-de]phthalazin-8-yl)benzaldehyde

HRID 907785Notes

Reaction equation

HRID 907785 reaction equation
C[O:2][CH:3](OC)[C:4]1[CH:9]=[CH:8][C:7]([CH:10]2[NH:22][C:20]3[C:21]4[C:12](=[N:13][NH:14][C:15](=[O:23])[C:16]=4[CH:17]=[CH:18][CH:19]=3)[CH:11]2[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[CH:6][CH:5]=1>Cl>[O:23]=[C:15]1[C:16]2[CH:17]=[CH:18][CH:19]=[C:20]3[NH:22][CH:10]([C:7]4[CH:6]=[CH:5][C:4]([CH:3]=[O:2])=[CH:9][CH:8]=4)[CH:11]([C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)[C:12]([C:21]=23)=[N:13][NH:14]1

Participants

3

Reactant 1

HCID 1363746658-(4-(Dimethoxymethyl)phenyl)-9-phenyl-8,9-dihydro-2H-pyrido[4,3,2-de]phthalazin-3(7H)-one

Product 1

HCID 1363447524-(3-Oxo-9-phenyl-3,7,8,9-tetrahydro-2H-pyrido[4,3,2-de]phthalazin-8-yl)benzaldehydeYield 73%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

To 8-(4-(dimethoxymethyl)phenyl)-9-phenyl-8,9-dihydro-2H-pyrido[4,3,2-de]phthalazin-3(7H)-one (89 mg, 0.22 mmol) was added 20 ml of hydrochloric acid (3 mol/L) and the mixture was stirred at room temperature for 2 h. The resulting mixture was evaporated under reduced pressure to 10 ml and then filtered, 59 mg of solid of 4-(3-oxo-9-phenyl-3,7,8,9-tetrahydro-2H-pyrido[4,3,2-de]phthalazin-8-yl)benzaldehyde was obtained; yield: 73%. LC-MS (ESI) m/z: 368 (M+1)+.

Workup

  1. customThe resulting mixture was evaporated under reduced pressure to 10 ml
  2. filtrationfiltered

Sources & evidence

ORD record
ord-17c9d0ded2e94f29ac4368245bb2d909
Source dataset
uspto-grants-2011_09
Patent number
US08012976B2

Reaction notes

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