HCID 19608221, compound → HCID 19607765, compound

HRID 1603136Notes

Reaction equation

HRID 1603136 reaction equation
[CH3:1][N:2]([CH3:26])[CH:3]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[N:7]([C:14](=[O:25])[C:15]2[CH:20]=[CH:19][C:18]([N+:21]([O-])=O)=[CH:17][C:16]=2[CH3:24])[CH2:6][CH2:5][CH2:4]1.[H][H]>C(O)C.[Pt]=O>[CH3:26][N:2]([CH3:1])[CH:3]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[N:7]([C:14](=[O:25])[C:15]2[CH:20]=[CH:19][C:18]([NH2:21])=[CH:17][C:16]=2[CH3:24])[CH2:6][CH2:5][CH2:4]1

Participants

5

Reactant 2

HCID 19608221HCID 19608221, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 19607765HCID 19607765, compoundYield 15.6%

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 702EthanolSolvent

Procedure

5-Dimethylamino-1-(2-methyl-4-nitrobenzoyl)-2,3,4,5-tetrahydro-1H-benzazepine (86.0 g) is dissolved in ethanol (800 ml), and thereto is added platinum oxide (10 g). The mixture is subjected to hydrogenation at ordinary temperature under atmospheric pressure of hydrogen for 4 hours. The catalyst is removed by filtration, and the solvent is distilled off. The resulting residue is purified by silica gel column chromatography (eluent; dichloromethane:methanol=200:1→100:1), and further purified by silica gel thin layer chromatography (developer; chloroform:methanol=10:1), and recrystallized from methanol/diethyl ether to give 5-dimethylamino-1-(2-methyl-4-aminobenzoyl)-2,3,4,5-tetrahydro-1H-benzazepine (G) (Rf: 0.52, 27.4 g) and 5-dimethylamino-1-(2-methyl-4-amino-benzoyl)-2,3,4,5-tetrahydro-1H-benzazepine (H) (Rf: 0.48, 12.3 g).

Workup

  1. customThe catalyst is removed by filtration
  2. distillationthe solvent is distilled off
  3. customThe resulting residue is purified by silica gel column chromatography (eluent; dichloromethane:methanol=200:1→100:1)
  4. customfurther purified by silica gel thin layer chromatography (developer; chloroform:methanol=10:1)
  5. customrecrystallized from methanol/diethyl ether

Sources & evidence

ORD record
ord-035a10475d2040fb851a411a8247343d
Source dataset
uspto-grants-1999_11
Patent number
US05985869

Reaction notes

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