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 1291676Notes

Reaction equation

HRID 1291676 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 3.0M 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-ba9a37f51f954692b0879ac6832d30b1
Source dataset
uspto-grants-1998_05
Patent number
US05753677

Reaction notes

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