Formaldehyde → HCID 23156817, compound

HRID 1098313Notes

Reaction equation

HRID 1098313 reaction equation
C=O.[C:3]([BH3-])#N.[Na+].[CH3:7][N:8]([CH3:31])[NH:9][C:10]1[CH:19]=[C:18]2[C:13]([CH:14]=[C:15]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[C:27]([F:30])([F:29])[F:28])[NH:16][C:17]2=[O:20])=[CH:12][CH:11]=1.C(=O)(O)[O-].[Na+]>CO.C(O)(=O)C>[F:29][C:27]([F:28])([F:30])[C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=1[C:15]1[NH:16][C:17](=[O:20])[C:18]2[C:13]([CH:14]=1)=[CH:12][CH:11]=[C:10]([N:9]([CH3:3])[N:8]([CH3:31])[CH3:7])[CH:19]=2

Participants

7

Reactant 4

HCID 712FormaldehydeHCID 516892Sodium BicarbonateHCID 5003444Sodium cyanoborohydrideHCID 23156736HCID 23156736, compound

Product 1

HCID 23156817HCID 23156817, compoundYield 88%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 887MethanolSolvent

Procedure

0.1 ml of acetic acid, 26.2 μl of a 37% formalin aqueous solution, and 25.3 mg (0.403 mmol) of sodium cyanoborohydride were added to 1 ml of a methanol solution containing 28 mg of the 7-(2,2-dimethylhydrazino)-3-(2-trifluoromethylphenyl)-2H-isoquinolin-1-one obtained in Example 149. The obtained mixture was stirred at a room temperature overnight. Thereafter, a saturated sodium bicarbonate aqueous solution was added to the reaction solution. The mixture was extracted with ethyl acetate, and was then dried over anhydrous sodium sulfate. The extract was concentrated. The obtained residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:2 to 2:1), so as to obtain 25.5 mg (88%) of 3-(2-trifluoromethylphenyl)-7-(1,2,2-trimethylhydrazino)-2H-isoquinolin-1-one in the form of a light yellow solid.

Workup

  1. extractionThe mixture was extracted with ethyl acetate
  2. dry with materialwas then dried over anhydrous sodium sulfate
  3. concentrationThe extract was concentrated
  4. customThe obtained residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:2 to 2:1)

Sources & evidence

ORD record
ord-0328e55f9a27489d83fe7a9751b6bf52
Source dataset
uspto-grants-2012_03
Patent number
US08143274B2

Reaction notes

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