Ammonium formate → HCID 59597227, compound

HRID 218589Notes

Reaction equation

HRID 218589 reaction equation
C([O:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[CH:15]([C:19]([N:21]([CH2:31][C:32]1[CH:37]=[CH:36][C:35]([N:38]([CH3:40])[CH3:39])=[CH:34][CH:33]=1)[C:22]1[CH:27]=[CH:26][C:25]([CH:28]([CH3:30])[CH3:29])=[CH:24][CH:23]=1)=[O:20])[CH2:14][CH2:13][CH2:12]2)C1C=CC=CC=1.C([O-])=O.[NH4+]>CO.[C].[Pd]>[CH3:39][N:38]([CH3:40])[C:35]1[CH:36]=[CH:37][C:32]([CH2:31][N:21]([C:22]2[CH:23]=[CH:24][C:25]([CH:28]([CH3:29])[CH3:30])=[CH:26][CH:27]=2)[C:19]([CH:15]2[C:16]3[C:11](=[CH:10][C:9]([OH:8])=[CH:18][CH:17]=3)[CH2:12][CH2:13][CH2:14]2)=[O:20])=[CH:33][CH:34]=1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 10186875HCID 10186875, compound

Product 1

HCID 59597227HCID 59597227, compoundYield 36.9%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

To a solution of 6-benzyloxy-N-[(4-dimethylaminophenyl)methyl]-N-(4-isopropylphenyl)-1,2,3,4-tetrahydronaphthalene-1-carboxamide (0.75 g) in methanol (8.6 mL) were added 10% palladium-carbon (0.09 g) and ammonium formate (0.44 g), and the mixture was stirred at room temperature for 24 hr. The reaction mixture was filtrated, and the solvent was evaporated. The obtained crude crystals were recrystallized from a mixed solvent of ethyl acetate and hexane to give N-[(4-dimethylaminophenyl)methyl]-6-hydroxy-N-(4-isopropylphenyl)-1,2,3,4-tetrahydronaphthalene-1-carboxamide (0.23 g). melting point: 169-171° C.

Workup

  1. filtrationThe reaction mixture was filtrated
  2. customthe solvent was evaporated
  3. customThe obtained crude crystals
  4. customwere recrystallized from a mixed solvent of ethyl acetate and hexane

Sources & evidence

ORD record
ord-17d6cd6b1563430384f9b63704465041
Source dataset
uspto-grants-2012_06
Patent number
US08198454B2

Reaction notes

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