O-Xylene → HCID 19006208, compound

HRID 1742914Notes

Reaction equation

HRID 1742914 reaction equation
[NH2:1][C:2]1[C:3]([F:16])=[CH:4][C:5]2[O:10][CH2:9][C:8](=[O:11])[N:7]([O:12][CH2:13][CH3:14])[C:6]=2[CH:15]=1.[C:17]1([CH3:24])[C:18]([CH3:23])=[CH:19][CH:20]=[CH:21][CH:22]=1>>[CH2:13]([O:12][N:7]1[C:6]2[CH:15]=[C:2]([N:1]3[CH:23]=[C:18]4[C:17]([CH2:22][CH2:21][CH2:20][CH2:19]4)=[CH:24]3)[C:3]([F:16])=[CH:4][C:5]=2[O:10][CH2:9][C:8]1=[O:11])[CH3:14]

Participants

3

Reactant 2

HCID 7237O-XyleneHCID 15219380HCID 15219380, compound

Product 1

HCID 19006208HCID 19006208, compound

Procedure

A mixture consisting of 6-amino-4-ethoxy-7-fluoro-1,4-benzoxazin -3(4H)-one (1.06 g), 1,2-cyclohexanedicarboxyaldehyde (0.7 g) and xylene (50 ml) was stirred for 15 minutes under heat-refluxing. After the solvent had been distilled off under reduced pressure, the residue was purified through silica-gel chromatography (eluent: hexane/ethyl acetate=19/1) to obtain the aimed 4-ethoxy-7-fluoro-6-(4,5,6,7-tetrahydroisoindole-2-yl)1,4-benzoxazin-3(4H)-one (1.37 g). nD20 1.5797

Workup

  1. temperatureunder heat-refluxing
  2. distillationAfter the solvent had been distilled off under reduced pressure
  3. customthe residue was purified through silica-gel chromatography (eluent: hexane/ethyl acetate=19/1)

Sources & evidence

ORD record
ord-3804a83873154a57b5b99d7bacc1fc42
Source dataset
uspto-grants-1994_08
Patent number
US05342938

Reaction notes

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