Hydrochloric Acid → HCID 21091024, compound

HRID 351262Notes

Reaction equation

HRID 351262 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:13]([C:14]3[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=3)[N:12]=[C:11]([C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH:10]=2)=[CH:5][CH:4]=1)#[N:2].[ClH:27]>C1COCC1.CO.[Pd]>[ClH:27].[NH2:2][CH2:1][C:3]1[CH:4]=[CH:5][C:6]([C:9]2[N:13]([C:14]3[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=3)[N:12]=[C:11]([C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH:10]=2)=[CH:7][CH:8]=1

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 21091028ethyl 5-(4-cyanophenyl)-1-(4-methoxyphenyl)-1H-pyrazole-3-carboxylate

Product 1

HCID 21091024HCID 21091024, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 10% Pd-C 50% wet (100 mg) and ethyl 5-(4-cyanophenyl)-1-(4-methoxyphenyl)-1H-pyrazole-3-carboxylate (1 g) in THF (10 ml), MeOH (5 ml), and 1M HCl (2.9 ml) was hydrogenated under H2 latmat ambient temperature for 6.5 hours. The catalyst was filtered off through a celite pad and the pad was washed with MeOH. The filtrate and combined washings were concentrated in vacuo. The residue was dissolved in EtOH and concentrated in vacuo. The residue was crystallized from AcOEt to give ethyl 5-[4-(aminomethyl)phenyl]-1-(4-methoxyphenyl)-1H-pyrazole-3-carboxylate hydrochloride (984 mg) as a powder.

Workup

  1. filtrationThe catalyst was filtered off through a celite pad
  2. washthe pad was washed with MeOH
  3. concentrationwere concentrated in vacuo
  4. dissolutionThe residue was dissolved in EtOH
  5. concentrationconcentrated in vacuo
  6. customThe residue was crystallized from AcOEt

Sources & evidence

ORD record
ord-27c98776ff2a4a328888a6a7498e7eec
Source dataset
uspto-grants-2007_02
Patent number
US07183306B2

Reaction notes

Loading…