Sodium Cyanide → Methyl 6-amino-1,3-benzodioxole-5-carboxylate

HRID 891267

Reaction equation

HRID 891267 reaction equation
C1OC2C=C([N+]([O-])=O)C(C=O)=CC=2O1.[CH2:15]1[O:27][C:26]2[CH:25]=[C:24]([N+:28]([O-])=O)[C:19]([C:20]([O:22][CH3:23])=[O:21])=[CH:18][C:17]=2[O:16]1.[C-]#N.[Na+]>CO.C(O)C.[O-2].[O-2].[Mn+4].[Pd]>[CH2:15]1[O:27][C:26]2[CH:25]=[C:24]([NH2:28])[C:19]([C:20]([O:22][CH3:23])=[O:21])=[CH:18][C:17]=2[O:16]1

Participants

8

Reactant 3

HCID 8929Sodium CyanideHCID 128406-Nitro-1,3-benzodioxole-5-carboxaldehydeHCID 697581,3-Benzodioxole-5-carboxylic acid, 6-nitro-, methyl ester2×

Product 1

HCID 290838Methyl 6-amino-1,3-benzodioxole-5-carboxylate

Reagents, catalysts & solvents 4

HCID 23938PalladiumCatalystHCID 178418406HCID 178418406, compoundCatalystHCID 702EthanolSolventHCID 887MethanolSolvent

Procedure

3,4-Methylenedioxy-6-nitrobenzaldehyde is converted to methyl 3,4-methylenedioxy-6-nitrobenzoate in methanol in the presence of sodium cyanide and manganese dioxide (Synthetic Commun., 27(7), 1281–1283 (1997)). Methyl 3,4-methylenedioxy-6-nitrobenzoate is hydrogenated in ethanol in the presence of palladium, 10% on carbon powder, at room temperature and atmospheric pressure to give methyl 3,4-methylenedioxy-6-amino-benzoate.

Sources & evidence

ORD record
ord-ceeee743870d4098918b30efb5a143e5
Source dataset
uspto-grants-2006_02
Patent number
US07002022B2

Linked notes

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