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Isoamyl Nitrite → 3-Methyl-4-(trifluoromethyl)benzonitrile

HRID 558472
Notes
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Reaction equation

HRID 558472 reaction equation
N[C:2]1[CH:9]=[C:8]([C:10]([F:13])([F:12])[F:11])[C:7]([CH3:14])=[CH:6][C:3]=1[C:4]#[N:5].N(OCCC(C)C)=O>C1COCC1.CC(OC)(C)C>[CH3:14][C:7]1[CH:6]=[C:3]([CH:2]=[CH:9][C:8]=1[C:10]([F:11])([F:12])[F:13])[C:4]#[N:5]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 8053Isoamyl Nitrite2×HCID 53416444HCID 53416444, compound

Product 1

HCID 574686963-Methyl-4-(trifluoromethyl)benzonitrile

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 15413tert-Butyl methyl etherSolvent

Conditions

Temperature
23 °C
On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Procedure

To a solution of 2-amino-5-methyl-4-trifluoromethyl-benzonitrile from step 4 (23.34 g, 117 mmol) in dry THF (350 mL) was added isoamyl nitrite (34.3 mL, 257 mmol), and the mixture was refluxed for 20 h. Additional isoamyl nitrite (16.6 mL, 129 mmol) was added and the mixture was refluxed for further 20 h. The mixture was cooled to 23° C. and diluted with TBME, the organic layer was washed with 1 N HCl, sat. NaHCO3-sol. and brine, dried over Na2SO4.

Workup

  1. temperaturethe mixture was refluxed for 20 h
  2. temperaturethe mixture was refluxed for further 20 h
  3. washthe organic layer was washed with 1 N HCl, sat. NaHCO3-sol
  4. dry with materialand brine, dried over Na2SO4

Sources & evidence

ORD record
ord-4c7aee1628d146aab935688e5024e29c
Source dataset
uspto-grants-2011_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08063048B2

Reaction notes

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