Formaldehyde → HCID 178482194, compound

HRID 1106256Notes

Reaction equation

HRID 1106256 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:20](=[O:21])[C:11]3=[CH:12][NH:13][C:14]4[CH:15]=[CH:16][CH:17]=[CH:18][C:19]=4[C:10]3=[N:9]2)=[CH:4][CH:3]=1.C=O.[C:24]([BH3-])#N.[Na+].C(#N)C>O.[OH-].[Na+].C(O)(=O)C>[CH3:24][NH:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:20](=[O:21])[C:11]3=[CH:12][NH:13][C:14]4[CH:15]=[CH:16][CH:17]=[CH:18][C:19]=4[C:10]3=[N:9]2)=[CH:4][CH:3]=1

Participants

8

Reactant 4

HCID 712FormaldehydeHCID 6342AcetonitrileHCID 5003444Sodium cyanoborohydrideHCID 178507701HCID 178507701, compound

Product 1

HCID 178482194HCID 178482194, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 14798Sodium HydroxideSolvent

Procedure

To the mixture of 1.4 g of 2-(p-aminophenyl)-pyrazolo-[4,3-c]quinolin-3(5H)-one, 4.1 ml of 37% aqueous formaldehyde, 1.0 g of sodium cyanoborohydride and 20 ml of acetonitrile, 0.6 g of glacial acetic acid are added while stirring. Stirring is continued overnight at room temperature and the mixture diluted with water. The precipitate formed is dissolved in diluted sodium hydroxide, the aqueous solution washed with diethyl ether and its pH adjusted to 8.5 by addition of aqueous ammonium chloride. The precipitate formed is collected, washed with methanol, then with diethyl ether and dried to yield the 2-(p-methylaminophenyl)-pyrazolo[4,3-c]quinolin-3(5H)-one melting at 302°-304°.

Workup

  1. additionare added
  2. stirringStirring
  3. customThe precipitate formed
  4. washthe aqueous solution washed with diethyl ether and its pH
  5. additionadjusted to 8.5 by addition of aqueous ammonium chloride
  6. customThe precipitate formed
  7. customis collected
  8. washwashed with methanol
  9. dry with materialwith diethyl ether and dried

Sources & evidence

ORD record
ord-0a35d5268397474486f4526317186729
Source dataset
uspto-grants-1982_01
Patent number
US04312870

Reaction notes

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