Carbon Dioxide → HCID 15043966, compound

HRID 2396343Notes

Reaction equation

HRID 2396343 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(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])=[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 3283Diethyl EtherSolventHCID 8857Ethyl AcetateSolvent

Procedure

Dissolve 3-nitro-2-carbethoxy-4,6-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 Celite and separate the organic phase of the filtrate. Dry (MgSO4) and evaporate the solvent in vacuo to give the title compoundas an off-yellow solid (33.5 g, 97.6%).

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-45a65de90ff1478b952565a666d0b2a6
Source dataset
uspto-grants-1996_02
Patent number
US05491153

Reaction notes

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