Formaldehyde → HCID 18677142, compound

HRID 1634093Notes

Reaction equation

HRID 1634093 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[C:14](N)=[CH:13][C:12]([C:16]([CH3:19])([CH3:18])[CH3:17])=[N:11]2)=[CH:6][CH:5]=1)([O-:3])=[O:2].[CH2:20]=O.[BH3-][C:23]#[N:24].[Na+].OS(O)(=O)=O>CO.C(O)(=O)C>[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[C:14]([N:24]([CH3:23])[CH3:20])=[CH:13][C:12]([C:16]([CH3:19])([CH3:18])[CH3:17])=[N:11]2)=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

7

Reactant 4

HCID 712FormaldehydeHCID 1118Sulfuric AcidHCID 13023603-tert-butyl-1-(4-nitrophenyl)-1H-pyrazol-5-amineHCID 5003444Sodium cyanoborohydride2×

Product 1

HCID 18677142HCID 18677142, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 887MethanolSolvent

Procedure

A mixture of 1-(4′-nitrophenyl)-3-t-butyl-5-aminopyrazole (I mmol) and formaldehyde (10 mmol, 37% w/w in H2O) in MeOH (7.5 mL) was stirred at rt for 30 minutes. Acetic acid (2.5 mL) and NaCNBH3 (2 mmol) were added, and after 1 hour additional NaCNBH3 (2 mmol) was added. After 1 hour, 1N H2SO4 was added, the solvent was removed and the residue was neutralized with NaHCO3. The solid product was collected by filtration, washed with water and dried to give 1-(4′-nitrophenyl)-3-t-butyl-5-dimethylaminopyrazole (0.265 g, 92%). Transfer hydrogenation of the nitro compound (0.89 mmol) as described in general in Method L gave 1-(4′-aminophenyl)-3-t-butyl-5-dimethylaminopyrazole (0.228 g, 100%).

Workup

  1. waitAfter 1 hour
  2. customthe solvent was removed
  3. filtrationThe solid product was collected by filtration
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-32ddff0fe66043c294b723e85d7cd4e5
Source dataset
uspto-grants-2003_01
Patent number
US06506747B1

Reaction notes

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