Ammonium formate → HCID 59597227, compound

HRID 2265358Notes

Reaction equation

HRID 2265358 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-612865ceb30e4b0fa94b28da974496dc
Source dataset
uspto-grants-2010_12
Patent number
US07855297B2

Reaction notes

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