Carbon Dioxide → HCID 21460704, compound

HRID 2396381Notes

Reaction equation

HRID 2396381 reaction equation
[N+:1]([C:4]1[C:12]2[C:7](=[CH:8][C:9]([Cl:14])=[C:10]([Cl:13])[CH:11]=2)[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(OCC)C.C(O)C.C(OCC)(=O)C>[NH2:1][C:4]1[C:12]2[C:7](=[CH:8][C:9]([Cl:14])=[C:10]([Cl:13])[CH:11]=2)[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 21460723HCID 21460723, compound

Product 1

HCID 21460704HCID 21460704, compound

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 3283Diethyl EtherSolventHCID 8857Ethyl AcetateSolvent

Procedure

Dissolve 3-nitro-2-carbethoxy-5,6-dichloroindole (38.1 g) in ethanol (1L) 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 intoa mixture of ethyl acetate (3L) and water (2L). Add solid potassium carbonate and stir occasionally until the carbon dioxide evolution ceases.Filter through diatomaceous earth and separate the organic phase of the filtrate. Dry (MgSO4) and evaporate the solvent in vacuo to give the title compound.

Workup

  1. temperatureWarm to between 65° and 75° C. for 4 to 5 hours
  2. additionpour
  3. customseparate the organic phase of the filtrate
  4. dry with materialDry (MgSO4)
  5. customevaporate the solvent in vacuo

Sources & evidence

ORD record
ord-80866b6cba0449f29cd8f3929c42d079
Source dataset
uspto-grants-1996_02
Patent number
US05491153

Reaction notes

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