Carbon Dioxide → HCID 15043966, compound

HRID 2082505Notes

Reaction equation

HRID 2082505 reaction equation
[N+:1]([C:4]1[C:12]2[C:7](=[CH:8][C:9]([Cl:14])=[CH:10][C:11]=2[Cl:13])[NH:6][C:5]=1[C:15]([O:17][CH2:18][CH3:19])=[O:16])([O-])=O.[Sn](Cl)Cl.C(=O)([O-])[O-].[K+].[K+].C(=O)=O>C(O)C.O.C(OCC)(=O)C>[NH2:1][C:4]1[C:12]2[C:7](=[CH:8][C:9]([Cl:14])=[CH:10][C:11]=2[Cl:13])[NH:6][C:5]=1[C:15]([O:17][CH2:18][CH3:19])=[O:16]

Participants

8

Reactant 4

HCID 280Carbon DioxideHCID 11430Potassium CarbonateHCID 24479Stannous ChlorideHCID 15043965HCID 15043965, compound

Product 1

HCID 15043966HCID 15043966, compoundYield 97.6%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

Dissolve 3-nitro-2-carbethoxy-4,6-dichloroindole (38.1 g) in ethanol (1 L) and add tin (II) chloride dehydrate (163 g). Warm to between 65° and 65° C. for 4 to 5 hours. Cool to room temperature and pour into a mixture of ethyl acetate (3 L) and water (2 L). Add solid potassium carbonate and stir occasionally until the carbon dioxide evolution ceases. Filter throught Celite and separate the organic phase of the filtrate. Dry (MgSO4) and evaporate the solvent in vacuo to give the title compound as an off-yellow solid (33.5 g, 97.6%).

Workup

  1. temperatureWarm to between 65° and 65° C. for 4 to 5 hours
  2. filtrationFilter
  3. customseparate the organic phase of the filtrate
  4. dry with materialDry (MgSO4)
  5. customevaporate the solvent in vacuo

Sources & evidence

ORD record
ord-c108f9c5d89b4dac8206d99fa6130f4c
Source dataset
uspto-grants-1993_02
Patent number
US05189054

Reaction notes

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