Methylamine → HCID 19609804, compound

HRID 2400769Notes

Reaction equation

HRID 2400769 reaction equation
[F:1][C:2]1[CH:9]=[C:8](F)[C:7]([F:11])=[CH:6][C:3]=1[C:4]#[N:5].[CH3:12][NH2:13]>C(O)C>[F:1][C:2]1[CH:9]=[C:8]([NH:13][CH3:12])[C:7]([F:11])=[CH:6][C:3]=1[C:4]#[N:5]

Participants

4

Reactant 2

HCID 6329MethylamineHCID 5938132,4,5-Trifluorobenzonitrile

Product 1

HCID 19609804HCID 19609804, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 2,4,5-trifluorobenzonitrile (0.575 g, 3.7 mmol) in ethanol (20 ml) was added methylamine (30% aq, 4.2 ml, 37 mmol) and the mixture stirred for 3 h. The reaction mixture was then partitioned between diethyl ether (100 ml) and water (100 ml), and the aqueous layer re-extracted with diethyl ether (100 ml). The combined ether extract was washed with brine (200 ml), dried (MgSO4) and evaporated to give 2,5-difluoro-4-methylaminobenzonitrile (0.549 g, 89%), mp 160-163° C.

Workup

  1. customThe reaction mixture was then partitioned between diethyl ether (100 ml) and water (100 ml)
  2. extractionthe aqueous layer re-extracted with diethyl ether (100 ml)
  3. extractionThe combined ether extract
  4. washwas washed with brine (200 ml)
  5. dry with materialdried (MgSO4)
  6. customevaporated

Sources & evidence

ORD record
ord-a714e77e20a047468063641a771c9357
Source dataset
uspto-grants-2014_08
Patent number
US08796277B2

Reaction notes

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