Carbon Dioxide → HCID 15043966, compound

HRID 1941416Notes

Reaction equation

HRID 1941416 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.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 61436Stannous chloride dihydrateHCID 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 dihydrate (163 g). Warm to between 65° and 75° 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 75° 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-6548370c6777458b93e499d0ebccaed6
Source dataset
uspto-grants-1997_12
Patent number
US05703107

Reaction notes

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