Sodium borohydride → HCID 178513739, compound

HRID 1049163Notes

Reaction equation

HRID 1049163 reaction equation
[OH:1][C:2]1[CH:27]=[CH:26][C:5]([CH:6]=[N:7][C:8]2[NH:12][N:11]=[C:10]([NH:13][C:14]3[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][CH:15]=3)[C:9]=2[C:23]([NH2:25])=[O:24])=[CH:4][CH:3]=1.[BH4-].[Na+]>CO>[OH:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][NH:7][C:8]2[NH:12][N:11]=[C:10]([NH:13][C:14]3[CH:15]=[CH:16][C:17]([N+:20]([O-:22])=[O:21])=[CH:18][CH:19]=3)[C:9]=2[C:23]([NH2:25])=[O:24])=[CH:26][CH:27]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 178513738HCID 178513738, compound

Product 1

HCID 178513739HCID 178513739, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

5-((4-hydroxybenzylidene)amino)-3-((4-nitrophenyl)amino)-1H-pyrazole-4-carboxamide (5.0 g) was suspended in 350 mL of MeOH and sodium borohydride was added until bubbling ceased. HPLC confirmed reaction was complete (absence of imine). Once completed (1 hr), precipitate was filtered to obtain 5-((4-hydroxybenzyl)amino)-3-((4-nitrophenyl)amino)-1H-pyrazole-4-carboxamide as an off white to light yellow powder. Product was washed with deionized water to remove excess sodium borohydride. Product was allowed to dry under vacuum for 18 hrs. 4.80 g (95% yield) of final product was obtained.

Workup

  1. customuntil bubbling
  2. customreaction
  3. custom(1 hr), precipitate
  4. filtrationwas filtered

Sources & evidence

ORD record
ord-901f7b2e68864038829d8c50500b6020
Source dataset
uspto-grants-2016_07
Patent number
US09382237B2

Reaction notes

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