Ammonium formate → N-[(4-dimethylaminophenyl)methyl]-5-hydroxy-N-(4-isopropylphenyl)-1,2,3,4-tetrahydronaphthalene-1-carboxamide

HRID 218570Notes

Reaction equation

HRID 218570 reaction equation
C([O:8][C:9]1[CH:18]=[CH:17][CH:16]=[C:15]2[C:10]=1[CH2:11][CH2:12][CH2:13][CH:14]2[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])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:27]=[CH:26][C:25]([CH:28]([CH3:29])[CH3:30])=[CH:24][CH:23]=2)[C:19]([CH:14]2[C:15]3[C:10](=[C:9]([OH:8])[CH:18]=[CH:17][CH:16]=3)[CH2:11][CH2:12][CH2:13]2)=[O:20])=[CH:33][CH:34]=1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 102801495-benzyloxy-N-[(4-dimethylaminophenyl)methyl]-N-(4-isopropylphenyl)-1,2,3,4-tetrahydronaphthalene-1-carboxamide

Product 1

HCID 10275167N-[(4-dimethylaminophenyl)methyl]-5-hydroxy-N-(4-isopropylphenyl)-1,2,3,4-tetrahydronaphthalene-1-carboxamideYield 80.2%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

5-Benzyloxy-N-[(4-dimethylaminophenyl)methyl]-N-(4-isopropylphenyl)-1,2,3,4-tetrahydronaphthalene-1-carboxamide (0.75 g) was dissolved in methanol (60 mL), and 10% palladium carbon (0.5 g) and ammonium formate (1.5 g) were added. The mixture was stirred at room temperature for one day. The reaction mixture was filtrated, and the filtrate was concentrated. Water was added to the residue, and the precipitated crude crystals were recrystallized from ethyl acetate to give N-[(4-dimethylaminophenyl)methyl]-5-hydroxy-N-(4-isopropylphenyl)-1,2,3,4-tetrahydronaphthalene-1-carboxamide (0.5 g). melting point: 200-202° C.

Workup

  1. filtrationThe reaction mixture was filtrated
  2. concentrationthe filtrate was concentrated
  3. additionWater was added to the residue
  4. customthe precipitated crude crystals
  5. customwere recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-2bd752c79eb14844af62961458efe573
Source dataset
uspto-grants-2012_06
Patent number
US08198454B2

Reaction notes

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