Potassium Sodium Tartrate → Methyl 5-amino-1-methyl-1h-indole-2-carboxylate
Reaction equation
[CH3:1][O:2][C:3]([C:5]1[N:6]([CH3:17])[C:7]2[C:12]([CH:13]=1)=[CH:11][C:10]([N+:14]([O-])=O)=[CH:9][CH:8]=2)=[O:4].O.O.Cl[Sn]Cl.[C@H](O)(C([O-])=O)[C@@H](O)C([O-])=O.[Na+].[K+].C([O-])(O)=O.[Na+]>CN(C=O)C>[CH3:1][O:2][C:3]([C:5]1[N:6]([CH3:17])[C:7]2[C:12]([CH:13]=1)=[CH:11][C:10]([NH2:14])=[CH:9][CH:8]=2)=[O:4]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 60 °C
Procedure
1-Methyl-5-nitro-1H-indole-2-carboxylic acid methyl ester (70 mg, 0.3 mmol) was dissolved in DMF (5 ml) and SnCl2.2H2O (339 mg, 1.5 mmol) was added as a solid. The resulting solution was stirred at 60° C. for 4 h. After cooling to room temperature, a pre-mixed aqueous solution of saturated Rochelle's salt (3 ml) and saturated NaHCO3 (3 ml) was added to the reaction mixture and the aqueous layer was extracted with EtOAc (3×6 ml). The organic layer was washed with H2O (3 ml), 1:1 NaHCO3:Rochelle's salt solution (3 ml), dried (MgSO4), filtered and the solvent was removed in vacuo to give the title compound.
Workup
- temperatureAfter cooling to room temperature
- extractionthe aqueous layer was extracted with EtOAc (3×6 ml)
- washThe organic layer was washed with H2O (3 ml), 1:1 NaHCO3
- dry with materialRochelle's salt solution (3 ml), dried (MgSO4)
- filtrationfiltered
- customthe solvent was removed in vacuo
Sources & evidence
- ORD record
- ord-e36ac9b3f41e4e89822ab6ef38d60512
- Source dataset
- uspto-grants-2008_02
- Patent number
- US07326732B2
Reaction notes
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