6,7-Methylenedioxyoxindole → 5H-[1,3]dioxolo[4,5-f]indole

HRID 4479Notes

Reaction equation

HRID 4479 reaction equation
[CH2:1]1[O:12][C:11]2[CH:10]=[C:9]3[C:5]([CH2:6][C:7](=O)[NH:8]3)=[CH:4][C:3]=2[O:2]1.[N+](C1C=C2OCOC2=CC=1CC(OC)=O)([O-])=O.[N+](C1OC2C(=C(CC(OC)=O)C=CC=2)O1)([O-])=O.C1OC2C(=C3C(=CC=2)NC(=O)C3)O1.C1OC2C(=CC=C3C=2NC(=O)C3)O1>>[CH2:1]1[O:12][C:11]2[CH:10]=[C:9]3[C:5]([CH:6]=[CH:7][NH:8]3)=[CH:4][C:3]=2[O:2]1

Participants

6

Reactant 5

HCID 212820116,7-MethylenedioxyoxindoleHCID 212820234,5-MethylenedioxyoxindoleHCID 212821015,6-MethylenedioxyoxindoleHCID 21282102Methyl 2-(6-nitrobenzo[d][1,3]dioxol-5-yl)acetateHCID 70406732Methyl 2-nitromethylenedioxyphenylacetate

Product 1

HCID 2607975H-[1,3]dioxolo[4,5-f]indole

Procedure

5,6-Methylenedioxyoxindole can be prepared via the reduction of methyl 2-nitro-4,5-methylenedioxyphenylacetate according to the procedure of McEvoy et al., J. Org. Chem., 38, 3350 (1973). By a similar procedure, starting with the appropriate methyl 2-nitromethylenedioxyphenylacetate, 4,5-methylenedioxyoxindole and 6,7-methylenedioxyoxindole are prepared.

Workup

  1. customare prepared

Sources & evidence

ORD record
ord-3ed5c8b0016f4432bfed93da605fb3ce
Source dataset
uspto-grants-1988_02
Patent number
US04725616

Reaction notes

Loading…