Formaldehyde → HCID 44818341, compound

HRID 1467573Notes

Reaction equation

HRID 1467573 reaction equation
[C:1]1([CH:7]2[NH:19][C:17]3[C:18]4[C:9](=[N:10][NH:11][C:12](=[O:20])[C:13]=4[CH:14]=[CH:15][CH:16]=3)[CH:8]2[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C=O.[C:29]([BH3-])#N.[Na+]>CO>[CH3:29][N:19]1[C:17]2[C:18]3[C:9](=[N:10][NH:11][C:12](=[O:20])[C:13]=3[CH:14]=[CH:15][CH:16]=2)[CH:8]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:7]1[C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 5003444Sodium cyanoborohydrideHCID 136186300HCID 136186300, compound

Product 1

HCID 44818341HCID 44818341, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 8,9-diphenyl-8,9-dihydro-2H-pyrido[4,3,2-de]phthalazin-3(7H)-one (1.04 mmol) in methanol (20 mL) is treated with formaldehyde (37 wt % in water, 270 μL, 3.61 mmol) at room temperature for overnight. Sodium cyanoborohydride (228 mg, 3.61 mmol) is added and the solution is stirred at room temperature for 3 h. After concentration under reduced pressure, the residue is dissolved in a mixture of trifluoroacetic acid and water and is purified by HPLC giving the 7-methyl-8,9-diphenyl-8,9-dihydro-2H-pyrido[4,3,2-de]phthalazin-3(7H)-one in good yield.

Workup

  1. concentrationAfter concentration under reduced pressure
  2. dissolutionthe residue is dissolved in a mixture of trifluoroacetic acid and water
  3. customis purified by HPLC

Sources & evidence

ORD record
ord-4c6bc874396443408fcc3c1841cbf987
Source dataset
uspto-grants-2015_04
Patent number
US08999987B2

Reaction notes

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