6-Nitro-1,3-benzodioxole-5-carboxaldehyde → 6-Aminobenzo[D][1,3]dioxole-5-carboxamide

HRID 1017511

Reaction equation

HRID 1017511 reaction equation
[CH2:1]1[O:11][C:10]2[C:3](=[CH:4][C:5]([N+:12]([O-])=O)=[C:6]([CH:9]=2)[CH:7]=[O:8])[O:2]1.O=[Cr](=O)(O[Cr](=O)([O-])=O)[O-].[NH+:24]1C=CC=CC=1.[NH+]1C=CC=CC=1>>[NH2:12][C:5]1[CH:4]=[C:3]2[O:2][CH2:1][O:11][C:10]2=[CH:9][C:6]=1[C:7]([NH2:24])=[O:8]

Participants

3

Reactant 2

HCID 128406-Nitro-1,3-benzodioxole-5-carboxaldehydeHCID 2724130Cornforth reagent

Product 1

HCID 107260536-Aminobenzo[D][1,3]dioxole-5-carboxamide

Procedure

The mixture of 4,5-methylenedioxy-2-nitrobenzaldehyde (12) (1.0 g, 5.1 mmol) and Cornforth reagent (CrO3-pyridine-water) (40 ml) was stirred under reflux for 4 h, and then evaporated. The solid was dissolved in water, and acidified with 10% HCl. The acidified solution was extracted with EtOAc, and dried over MgSO4. After evaporation, the solid was treated as described for the preparation of 10 to afford 16 (0.7 g) as brown powder; MS m/z 180 (M+).

Workup

  1. temperatureunder reflux for 4 h
  2. customevaporated
  3. dissolutionThe solid was dissolved in water
  4. extractionThe acidified solution was extracted with EtOAc
  5. dry with materialdried over MgSO4
  6. customAfter evaporation
  7. additionthe solid was treated
  8. customas described for the preparation of 10

Sources & evidence

ORD record
ord-ec98cb78c4c44e769756742f51161f61
Source dataset
uspto-grants-2002_11
Patent number
US06479499B1

Linked notes

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