Ammonia → HCID 59334995, compound

HRID 1517959Notes

Reaction equation

HRID 1517959 reaction equation
[N+:1]([C:4]1[CH:12]=[C:11]2[C:7]([C:8]([C:13]([OH:15])=O)=[CH:9][NH:10]2)=[CH:6][CH:5]=1)([O-:3])=[O:2].S(Cl)(Cl)=O.[NH3:20]>C1(C)C=CC=CC=1.ClCCl.O1CCCC1.O1CCOCC1>[N+:1]([C:4]1[CH:12]=[C:11]2[C:7]([C:8]([C:13]([NH2:20])=[O:15])=[CH:9][NH:10]2)=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

8

Reactant 3

HCID 222AmmoniaHCID 24386Thionyl ChlorideHCID 2560996-nitro-1h-indole-3-carboxylic acid

Product 1

HCID 59334995HCID 59334995, compound

Reagents, catalysts & solvents 4

HCID 1140TolueneSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
60 °C

Procedure

250 mg 6-nitro-1H-indole-3-carboxylic acid are dissolved in 10 ml of toluene, combined with 3 ml of thionyl chloride and refluxed for 1 hour. Then the volatile constituents are eliminated in vacuo, the residue is taken up in dichloromethane and this is in turn eliminated in vacuo. Then it is taken up in 10 ml of tetrahydrofuran, combined with 6 ml of a 0.5 M solution of ammonia in dioxane and heated to 60° C. for 12 hours. The solvents are eliminated in vacuo, the residue is extracted from 1 N hydrochloric acid and the solid obtained is suction filtered and dried in vacuo.

Workup

  1. temperaturerefluxed for 1 hour
  2. extractionthe residue is extracted from 1 N hydrochloric acid
  3. customthe solid obtained
  4. filtrationfiltered
  5. customdried in vacuo

Sources & evidence

ORD record
ord-5600892f99204fe89eb98c798a31c2a6
Source dataset
uspto-grants-2012_07
Patent number
US08232312B2

Reaction notes

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