Hydrochloric Acid → 5-amino-1-(2-hydroxyethyl)-1H-pyrazole-4-carbaldehyde

HRID 349547Notes

Reaction equation

HRID 349547 reaction equation
[NH2:1][C:2]1[N:6]([CH2:7][CH2:8][OH:9])[N:5]=[CH:4][C:3]=1[C:10]#N.Cl.C[OH:14]>[C].[Pd]>[NH2:1][C:2]1[N:6]([CH2:7][CH2:8][OH:9])[N:5]=[CH:4][C:3]=1[CH:10]=[O:14]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 2198525-amino-1-(2-hydroxyethyl)-1H-pyrazole-4-carbonitrile

Product 1

HCID 179620345-amino-1-(2-hydroxyethyl)-1H-pyrazole-4-carbaldehyde

Reagents, catalysts & solvents 1

HCID 178418390HCID 178418390, compoundCatalyst

Procedure

To a solution of 5-amino-1-(2-hydroxyethyl)-1H-pyrazole-4-carbonitrile (15 g) in methanol (300 ml) was added hydrochloric acid (1.8 ml) under ice-cooling. The resulting solution was stirred for 15 minutes. The mixture was treated with 10% palladium carbon (7.5 g) under a hydrogen atmosphere at room temperature for 3 hours. After the catalyst was filtered off, the filtrate was concentrated in vacuo to give 5-amino-1-(2-hydroxyethyl)-1H-pyrazole-4-carbaldehyde (13.3 g).

Workup

  1. temperaturecooling
  2. filtrationAfter the catalyst was filtered off
  3. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-67e106826f9c4d3fac004ef6ef0484cf
Source dataset
uspto-grants-2007_02
Patent number
US07179801B2

Reaction notes

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