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Water → 2-(trifluoromethyl)-1H-indole-5-carbonitrile

HRID 2061559
Notes
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Reaction equation

HRID 2061559 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7]([C:12]([F:15])([F:14])[F:13])=[C:6]2C(O)=O)#[N:2].O>CN1C(=O)CCC1>[F:15][C:12]([F:13])([F:14])[C:7]1[NH:8][C:9]2[C:5]([CH:6]=1)=[CH:4][C:3]([C:1]#[N:2])=[CH:11][CH:10]=2
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 962Water2×HCID 581389305-cyano-2-(trifluoromethyl)-1H-indole-3-carboxylic acid2×

Product 1

HCID 581268122-(trifluoromethyl)-1H-indole-5-carbonitrileYield 82.2%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
135 °C

Procedure

5-cyano-2-(trifluoromethyl)-1H-indole-3-carboxylic acid (Intermediate 13, 2.09 g) was dissolved in NMP (10 mL) and H2O (1 mL) was then added. The mixture was heated to 130-140° C. overnight under nitrogen. The solution was cooled to room temperature and H2O (30 mL) was added and the solution stirred for 40 min. and then filtered. The cake was washed with H2O. The product is then dried under vacuum at 40° C. to give the title compound (1.42 g);

Workup

  1. temperatureThe solution was cooled to room temperature
  2. filtrationfiltered
  3. washThe cake was washed with H2O
  4. customThe product is then dried under vacuum at 40° C.

Sources & evidence

ORD record
ord-a5d6f8507c3b4b8d9e6d0f644a062501
Source dataset
uspto-grants-2012_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08283365B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes