Water → 2-Chlorodibenz(b,f)-1,4-oxazepin-11(10H)-one

HRID 2180915Notes

Reaction equation

HRID 2180915 reaction equation
[N+:1]([C:4]1[CH:9]=[C:8]([Cl:10])[CH:7]=[CH:6][C:5]=1[O:11][C:12](=O)[C:13]1[C:14](=[CH:16][CH:17]=[CH:18][CH:19]=1)[OH:15])([O-])=O.O>CO.[Ni].C1(C)C(C)=CC=CC=1>[Cl:10][C:8]1[CH:7]=[CH:6][C:5]2[O:11][C:12]3[CH:13]=[CH:19][CH:18]=[CH:17][C:16]=3[C:14](=[O:15])[NH:1][C:4]=2[CH:9]=1

Participants

6

Reactant 2

HCID 962WaterHCID 68807913HCID 68807913, compound

Product 1

HCID 766192-Chlorodibenz(b,f)-1,4-oxazepin-11(10H)-oneYield 47.1%

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 887MethanolSolvent2×HCID 7237O-XyleneSolvent2×

Procedure

A solution of 33.74 g of O-(2-nitro-4-chlorophenyl)salicylic acid in 150 mL of methanol was hydrogenated over Raney nickel (6.8 g) at room temperature and 30 psi pressure with stirring for 20 hours. The crude amino acid obtained on evaporation of the methanol was refluxed in 150 mL of xylene for 20 hours with continuous removal of water. The xylene solution was cooled and the xylene was removed, the residue was washed with THF, filtered and dried to provide 8-chloro-10H-dibenzo[b,f][1,4]oxazepin-11-one as gray solid (13.3 g, 40%), mp 260-261°. 1H NMR (300 MHz, DMSO-d6), δ 7.15-7.2 (m, 2H), 7.3-7.4 (m, 3H), 7.64 (ddd, 1H, J=1.9, 7.8 and 8.4 Hz), 7.78 (dd, 1H, J=1.5 and 7.7 Hz), 10.589 (s, 1H, —NH).

Workup

  1. customthe xylene was removed
  2. washthe residue was washed with THF
  3. filtrationfiltered
  4. customdried

Sources & evidence

ORD record
ord-ace065a2da2c4dbbbb721fd313d9ba7c
Source dataset
uspto-grants-2005_05
Patent number
US06890919B2

Reaction notes

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