Methylamine → HCID 59529818, compound

HRID 1410258Notes

Reaction equation

HRID 1410258 reaction equation
[CH3:1][NH2:2].[CH2:3]([O:5][C:6](=[O:18])[C:7]1[CH:12]=[C:11]([N+:13]([O-:15])=[O:14])[C:10](F)=[CH:9][C:8]=1[F:17])[CH3:4]>C1COCC1>[F:17][C:8]1[CH:9]=[C:10]([NH:2][CH3:1])[C:11]([N+:13]([O-:15])=[O:14])=[CH:12][C:7]=1[C:6]([O:5][CH2:3][CH3:4])=[O:18]

Participants

4

Reactant 2

HCID 6329MethylamineHCID 22330120Ethyl 2,4-difluoro-5-nitrobenzoate

Product 1

HCID 59529818HCID 59529818, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A 2N solution of methylamine in THF (11.5 ml, 23.0 mmol) was added at −5° C. to ethyl-2,4-difluoro-5-nitro-benzoate (2.50 g, 10.8 mmol) in 20 ml THF and the cooling bath was removed. After 15 min at room temperature, the mixture was concentrated i.vac., 50 ml DCM were added, the organic phase was washed with water and dried with MgSO4. After concentration i.vac. the crude product was triturated with ethanol to give the cristalline product.

Workup

  1. customthe cooling bath was removed
  2. concentrationthe mixture was concentrated i.vac
  3. addition, 50 ml DCM were added
  4. washthe organic phase was washed with water
  5. dry with materialdried with MgSO4
  6. concentrationAfter concentration i.vac
  7. customthe crude product was triturated with ethanol
  8. customto give the cristalline product

Sources & evidence

ORD record
ord-bf7ea3a5543c492f8cafc13e0ad03de1
Source dataset
uspto-grants-2014_12
Patent number
US08921405B2

Reaction notes

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