Methylamine → 6-Bromo-2-methylamino-1-nitronaphthalene

HRID 1709211Notes

Reaction equation

HRID 1709211 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8]([N+:12]([O-:14])=[O:13])=[C:7](OC)[CH:6]=[CH:5]2.[CH3:17][NH2:18]>CN(C)C=O>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8]([N+:12]([O-:14])=[O:13])=[C:7]([NH:18][CH3:17])[CH:6]=[CH:5]2

Participants

4

Reactant 2

HCID 6329Methylamine2×HCID 220971876-Bromo-2-methoxy-1-nitronaphthalene

Product 1

HCID 198278026-Bromo-2-methylamino-1-nitronaphthalene

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 6-bromo-2-methoxy-1-nitronaphthalene (5.64 g, 20 mmol) in 100 ml of dry N,N-dimethylformamide saturated with methylamine was stirred in a stoppered flask at 80° C. for 4 h. During the reaction period the mixture was saturated twice with a further quantity of methylamine. The cooled mixture was poured into 1 1 of ice/water. After stirring for 1 h, the orange solid was collected by filtration and washed with water, and dried in vacuo over phosphorus pentoxide affording 5.43 g (96%) of the title compound. M.p. 169°-170 ° C.: 1H-NMR (CDCl3): 3.11 (d, J=5 Hz, 3H, CH3), 7.00 (d, J=9 Hz, 1H, ArH), 7.45-7.78 (m, 3H, ArH), 8.60 (d, J=9 Hz, 1H, ArH), 8.7 (broad, 1H, NH).

Workup

  1. customDuring the reaction period the mixture
  2. filtrationthe orange solid was collected by filtration
  3. washwashed with water
  4. dry with materialdried in vacuo over phosphorus pentoxide affording 5.43 g (96%) of the title compound

Sources & evidence

ORD record
ord-e2949e4435804fe4b6849e310e52e7b1
Source dataset
uspto-grants-1990_08
Patent number
US04948794

Reaction notes

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