Methylamine → HCID 53401485, compound

HRID 1890481Notes

Reaction equation

HRID 1890481 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[C:4](F)[CH:3]=1.[CH:12]([N:15](CC)C(C)C)(C)C.CN.CN.C1COCC1>C1COCC1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[C:4]([CH2:12][NH2:15])[CH:3]=1

Participants

6

Reactant 4

HCID 6329MethylamineHCID 81531DiisopropylethylamineHCID 27833624-Bromo-2-fluoro-1-nitrobenzeneHCID 66615946Methylamine tetrahydrofuran

Product 1

HCID 53401485HCID 53401485, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
105 °C

Procedure

A solution of 4-bromo-2-fluoronitrobenzene (1.2 g) in THF (10 ml) is heated in the presence of N,N-diisopropylethylamine (690 μl) and of methylamine (2M in THF, 3 ml) in a microwave reactor (10° C., 20 min). After 20 min, 100 μl of methylamine THF (2M) are added and the resulting mixture is heated at 105° C. for a further 5 minutes. The reaction medium is concentrated and then taken up in ethyl acetate, and washed with water and then with brine. The organic extracts are combined, dried over magnesium sulphate, filtered and evaporated under reduced pressure. (5-Bromo-2-nitrophenyl)methylamine (1.2 g) is isolated in the form of an orange solid which 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-52edfdd04a9145d08b2901f6ba18e7cd
Source dataset
uspto-grants-2013_08
Patent number
US08507483B2

Reaction notes

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