Toluene → HCID 68979461, compound

HRID 2035417Notes

Reaction equation

HRID 2035417 reaction equation
[CH:1]1[C:11]2[C:10](=[O:12])[C:9]3[CH:13]=[CH:14][CH:15]=[CH:16][C:8]=3[C:7](=[O:17])[NH:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.[C:18]1(C)C=CC=CC=1.[Cl-].[NH4+]>>[OH:12][C:10]1([CH3:18])[C:9]2[CH:13]=[CH:14][CH:15]=[CH:16][C:8]=2[C:7](=[O:17])[NH:6][C:5]2[CH:4]=[CH:3][CH:2]=[CH:1][C:11]1=2

Participants

4

Reactant 3

HCID 1140TolueneHCID 25517Ammonium ChlorideHCID 708365H-Dibenz(b,e)azepine-6,11-dione

Product 1

HCID 68979461HCID 68979461, compoundYield 98%

Procedure

To a suspension of 5H-dibenzo[b,e]azepine-6,11-dione (2) (50 g, 0.22 mol) in toluene (800 mL) methyl magnesium iodide (3 M in Et2O, 200 mL, 0.6 mol) was added. The reaction mixture was heated under reflux for 6 h, then poured into aqueous ammonium chloride and stirred for 10 minutes. The product was filtered off and dried to give 11-hydroxy-11-methyl-5,11-dihydro-dibenzo[b,e]azepin-6-one (3) as a white solid (51.6 g, 96%). Data: (m/z)=240 (M+H)+.

Workup

  1. additionwas added
  2. temperatureThe reaction mixture was heated
  3. temperatureunder reflux for 6 h
  4. filtrationThe product was filtered off
  5. customdried

Sources & evidence

ORD record
ord-5ab3e8e9eb804d0fb28501441508125a
Source dataset
uspto-grants-2013_11
Patent number
US08575152B2

Reaction notes

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