Potassium Carbonate → HCID 136374692, compound

HRID 1968006Notes

Reaction equation

HRID 1968006 reaction equation
C([O:3][CH:4](OCC)[C:5]1[CH:6]=[C:7]([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]2C2C=CC=C(C(OCC)OCC)C=2)[CH:8]=[CH:9][CH:10]=1)C.[C:41](=[O:44])([O-])[O-].[K+].[K+]>Cl>[O:24]=[C:16]1[C:17]2[CH:18]=[CH:19][CH:20]=[C:21]3[NH:23][C:11]([C:7]4[CH:6]=[C:5]([CH:10]=[CH:9][CH:8]=4)[CH:4]=[O:3])([C:5]4[CH:10]=[C:9]([CH:8]=[CH:7][CH:6]=4)[CH:41]=[O:44])[CH2:12][C:13]([C:22]=23)=[N:14][NH:15]1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 136374685HCID 136374685, compound

Product 1

HCID 136374692HCID 136374692, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A mixture of 8,9-bis(3-(diethoxymethyl)phenyl)-8,9-dihydro-2H-pyrido[4,3,2-de]phthalazin-3(7H)-one (120 mg, 0.46 mmol) in 3N hydrochloric acid (5 mL) was stirred at room temperature for 2 hr. Then the mixture was adjusted to pH=8 with potassium carbonate. The resulting suspension was filtered to give 3,3′-(3-oxo-3,7,8,9-tetrahydro-2H-pyrido[4,3,2-de]phthalazin-8,8-diyl)dibenzaldehyde (160 mg, yield 88%) as a light yellow solid. 1H-NMR (400 MHz, DMSO-d6) δ (ppm): 4.57-4.59 (d, J=9.6 Hz, 1H), 4.98-5.00 (d, J=9.2 Hz, 1H), 7.20-7.22 (d, J=7.6 Hz, 1H), 7.42-7.52 (m, 5H), 7.60-7.77 (m, 5H), 7.89 (s, 1H), 9.90 (s, 1H), 9.93 (s, 1H), 12.08 (s, 1H); LC-MS (ESI) m/z: 396 (M+1)+.

Workup

  1. filtrationThe resulting suspension was filtered

Sources & evidence

ORD record
ord-9ed2a55240b64bc989128271a41bc60e
Source dataset
uspto-grants-2013_04
Patent number
US08420650B2

Reaction notes

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