Dichloromethane → HCID 19021685, compound

HRID 1108993Notes

Reaction equation

HRID 1108993 reaction equation
O[C:2]1[C:3]([O:22][CH3:23])=[CH:4][C:5]2[CH2:6][C:7]3[C:8]([C:20]=2[CH:21]=1)=[N:9][C:10]1[CH:11]=[C:12]2[O:19][CH2:18][O:17][C:13]2=[CH:14][C:15]=1[CH:16]=3.C(Cl)Cl.[CH3:27][N:28]=[C:29]=[O:30]>CN(C)C1C=CN=CC=1>[CH3:27][NH:28][C:29]([C:2]1[C:3]([O:22][CH3:23])=[CH:4][C:5]2[CH2:6][C:7]3[C:8]([C:20]=2[CH:21]=1)=[N:9][C:10]1[CH:11]=[C:12]2[O:19][CH2:18][O:17][C:13]2=[CH:14][C:15]=1[CH:16]=3)=[O:30]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 12228Methyl IsocyanateHCID 15227805HCID 15227805, compound

Product 1

HCID 19021685HCID 19021685, compound

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Conditions

Temperature
0 °C

Procedure

Compound 8, prepared in Example 8, (308 mg, 1 mmol), anhydrous methylene chloride (5 mL), 4-dimethylamino pyridine (489 mg, 4 mmol) and methyl isocyanate (171 mg, 0.18 mmol) are stirred at about 0° C. under a dry nitrogen atmosphere for about an hour. The reaction is allowed to cool to ambient temperature. Stirring is continued for about 16 hrs. while maintaining the nitrogen atmosphere. The solvent is then removed by reduced pressure evaporation to give a solid residue. This residue is chromatographed (silica gel eluded with ethyl acetate) to yield 7-n-Methylcarbamoyl-8-methoxy-10H-1,3-dioxolo[4,5-g]indeno[1,2-b]quinoline

Workup

  1. temperatureto cool to ambient temperature
  2. stirringStirring
  3. temperaturewhile maintaining the nitrogen atmosphere
  4. customThe solvent is then removed by reduced pressure evaporation
  5. customto give a solid residue
  6. customThis residue is chromatographed (silica gel eluded with ethyl acetate)

Sources & evidence

ORD record
ord-e72c73f105514990ba90ec97f099aabd
Source dataset
uspto-grants-1994_06
Patent number
US05318976

Reaction notes

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