Methylamine → (2-Bromo-6-nitrophenyl)methanamine

HRID 1890487Notes

Reaction equation

HRID 1890487 reaction equation
[Br:1][C:2]1[C:3](F)=[C:4]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:6][CH:7]=1.[CH:12]([N:15](CC)C(C)C)(C)C.CN>C1COCC1>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([N+:8]([O-:10])=[O:9])[C:3]=1[CH2:12][NH2:15]

Participants

5

Reactant 3

HCID 6329MethylamineHCID 81531DiisopropylethylamineHCID 404274461-Bromo-2-fluoro-3-nitrobenzene

Product 1

HCID 66926623(2-Bromo-6-nitrophenyl)methanamine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 3-bromo-2-fluoronitrobenzene (1 g) in THF (8.3 ml) is heated in the presence of N,N-diisopropylethylamine (690 μA) and of methylamine (2.54 ml) in a microwave reactor (105° C., 30 min). The reaction medium is concentrated and then taken up in ethyl acetate, and then washed with water and then with brine. The organic extracts are combined, dried over magnesium sulphate, filtered and evaporated under reduced pressure. (2-Bromo-6-nitrophenyl)methylamine (1 g) is isolated in the form of an orange solid, and is used as it is in the next stage.

Workup

  1. concentrationThe reaction medium is concentrated
  2. washwashed with water
  3. dry with materialdried over magnesium sulphate
  4. filtrationfiltered
  5. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-c63e8ab86e0945a2a805375bb0fd986d
Source dataset
uspto-grants-2013_08
Patent number
US08507483B2

Reaction notes

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