Ammonia → 6-Bromo-1-nitronaphthalen-2-amine

HRID 1751626Notes

Reaction equation

HRID 1751626 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.C[N:18](C)C=O.N.O>CO>[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]([NH2:18])[CH:6]=[CH:5]2

Participants

6

Reactant 4

HCID 222AmmoniaHCID 962WaterHCID 6228DimethylformamideHCID 220971876-Bromo-2-methoxy-1-nitronaphthalene

Product 1

HCID 218071856-Bromo-1-nitronaphthalen-2-amineYield 95%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
130 °C

Procedure

6-bromo-2-methoxy-1-nitronaphthalene (12.6 g, 44.7 mmol), dimethylformamide (25.6 mL) and 7N NH3 solution in MeOH (128 mL, purchased from Sigma Aldrich) were combined in a Parr bomb. The bomb was heated in a lab oven at 130° C. After 48 hours, the reactor was removed from the oven and cooled to room temperature. The contents of the bomb were transferred to a glass round bottom flask. The bomb was thoroughly rinsed with dichloromethane and methanol, and the rinsings added to the flask. The contents of the flask were thoroughly concentrated on a rotary evaporator, leaving a brown solid. Water (200 mL) was added to the flask and the resulting suspension was agitated with a stir bar for 30 minutes. The resulting light brown powder was isolated by filtration, rinsing a few times with water. The filter cake was air dried over night to yield 6-bromo-1-nitronaphthalen-2-amine (11.6 g, >95% yield).

Workup

  1. customthe reactor was removed from the oven
  2. temperaturecooled to room temperature
  3. customThe contents of the bomb were transferred to a glass round bottom flask
  4. washThe bomb was thoroughly rinsed with dichloromethane and methanol
  5. additionthe rinsings added to the flask
  6. concentrationThe contents of the flask were thoroughly concentrated on a rotary evaporator
  7. customleaving a brown solid
  8. customThe resulting light brown powder was isolated by filtration
  9. washrinsing a few times with water
  10. customdried over night

Sources & evidence

ORD record
ord-9149a1d131d54949801440a2161045ca
Source dataset
uspto-grants-2015_10
Patent number
US09156823B2

Reaction notes

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