2-Methyl-N-[4-[(2,3,4,5-tetrahydro-5-oxo-1H-1-benzazepin-1-yl)carbonyl]phenyl]benzamide → 5-methyl-5-hydroxy-1-[4-(2-methylbenzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-benzazepine

HRID 1603155Notes

Reaction equation

HRID 1603155 reaction equation
[O:1]=[C:2]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[N:6]([C:13](=[O:30])[C:14]2[CH:19]=[CH:18][C:17]([NH:20][C:21](=[O:29])[C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[CH3:28])=[CH:16][CH:15]=2)[CH2:5][CH2:4][CH2:3]1.[CH3:31][Mg]Br>O1CCCC1.C(OCC)C>[CH3:31][C:2]1([OH:1])[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[N:6]([C:13](=[O:30])[C:14]2[CH:19]=[CH:18][C:17]([NH:20][C:21](=[O:29])[C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[CH3:28])=[CH:16][CH:15]=2)[CH2:5][CH2:4][CH2:3]1

Participants

5

Reactant 2

HCID 108108812-Methyl-N-[4-[(2,3,4,5-tetrahydro-5-oxo-1H-1-benzazepin-1-yl)carbonyl]phenyl]benzamideHCID 178418573HCID 178418573, compound

Product 1

HCID 196078505-methyl-5-hydroxy-1-[4-(2-methylbenzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-benzazepine

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

5-Oxo-1-[4-(2-methylbenzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-benzazepine (0.50 g) is suspended in tetrahydrofuran (20 ml), and thereto is added dropwise a 3.0 M solution of methyl magnesium bromide in diethyl ether (1.5 ml) at room temperature. The mixture is stirred at room temperature for 1 hour. The reaction solution is poured into ice-water (20 ml), and extracted with ethyl acetate. The extract is dried over magnesium sulfate, and the solvent is distilled off. The resulting residue is purified by silica gel column chromatography (eluent; ethyl acetate:n-hexane=2:3→1:1), and recrystallized from ethyl acetate/n-hexane to give 5-methyl-5-hydroxy-1-[4-(2-methylbenzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-benzazepine (0.23 g) as white powder, m.p. 204-205° C.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe extract is dried over magnesium sulfate
  3. distillationthe solvent is distilled off
  4. customThe resulting residue is purified by silica gel column chromatography (eluent; ethyl acetate:n-hexane=2:3→1:1)
  5. customrecrystallized from ethyl acetate/n-hexane

Sources & evidence

ORD record
ord-d8b0572e02e34cd7a73fd9d8c65871b2
Source dataset
uspto-grants-1999_11
Patent number
US05985869

Reaction notes

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