Ammonia → 5-trifluoromethoxy-1H-indole-2-carboxylic acid amide

HRID 1392233Notes

Reaction equation

HRID 1392233 reaction equation
C(Cl)(=O)C(Cl)=O.[F:7][C:8]([F:23])([F:22])[O:9][C:10]1[CH:11]=[C:12]2[C:16](=[CH:17][CH:18]=1)[NH:15][C:14]([C:19](O)=[O:20])=[CH:13]2.[NH3:24]>C1COCC1.CN(C)C=O>[F:7][C:8]([F:23])([F:22])[O:9][C:10]1[CH:11]=[C:12]2[C:16](=[CH:17][CH:18]=1)[NH:15][C:14]([C:19]([NH2:24])=[O:20])=[CH:13]2

Participants

6

Reactant 3

HCID 222AmmoniaHCID 65578Oxalyl chlorideHCID 27772905-(Trifluoromethoxy)-1H-indole-2-carboxylic acid

Product 1

HCID 692204685-trifluoromethoxy-1H-indole-2-carboxylic acid amide

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
2.5 °C

Procedure

Oxalyl chloride (2.63 ml, 30.6 mmol) was added dropwise at 0° C. within 45 min. to a suspension of 5-trifluoromethoxy-1H-indole-2-carboxylic acid (5 g, 20.4 mmol) in THF (20 ml) and N,N-dimethyl formamide (0.5 ml). Stirring was continued at 0-5° C. for 30 min. and thereafter for 3 h at room temperature. The resulting solution was cooled to 0-5° C. again and then added within 15 min. to 75 ml of a 25% aqueous solution of ammonia. After stirring for 30 min. the precipitated amide was collected, washed with water and dried at 40° C. in vacuo yielding 5-trifluoromethoxy-1H-indole-2-carboxylic acid amide as off white solid. Yield 5 g (100%)

Workup

  1. waitfor 3 h at room temperature
  2. customwas collected
  3. washwashed with water
  4. customdried at 40° C. in vacuo

Sources & evidence

ORD record
ord-1dacd341192f45c2af9a533f0eb0a81b
Source dataset
uspto-grants-2008_03
Patent number
US07342030B2

Reaction notes

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