Bromine → HCID 67004539, compound

HRID 1929593Notes

Reaction equation

HRID 1929593 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[CH:13]=[CH:12][C:10]([NH2:11])=[C:9]([N+:14]([O-:16])=[O:15])[CH:8]=2)[CH:2]=1.[Br:17]Br>CC(O)=O>[Br:17][C:12]1[CH:13]=[C:7]([C:3]2[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=2)[CH:8]=[C:9]([N+:14]([O-:16])=[O:15])[C:10]=1[NH2:11]

Participants

4

Reactant 2

HCID 24408BromineHCID 104658594-(Pyridin-3-yl)-2-nitroaniline

Product 1

HCID 67004539HCID 67004539, compoundYield 30.2%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

To a solution of 4-(pyridin-3-yl)-2-nitroaniline (1.3 g, 9 mmol) in HOAc (25 mL) was added bromine (1.58 g, 9.9 mmol) in HOAc (5 mL). The resulting mixture was stirred at room temperature for one hour and then quenched with ice-water. The solids were collected, washed with water and dried. The solids in EtOAc was then washed with NaOH (2N; 20 mL), water, brine and concentrated in vacuo. The concentrate was purified by chromatography [Silica Gel, ethyl acetate:hexanes (1:1)] to afford the title compound (0.8 g). 1H NMR (CDCl3) δ 8.83 (d, 1H), 8.55 (m, 1H), 8.41 (d, 1H), 8.15 (d, 1H), 7.96 (m, 1H), 7.41 (m, 1H), 6.80 (br s, 2H). (M+1) 294.

Workup

  1. customquenched with ice-water
  2. customThe solids were collected
  3. washwashed with water
  4. customdried
  5. washThe solids in EtOAc was then washed with NaOH (2N; 20 mL), water, brine
  6. concentrationconcentrated in vacuo
  7. customThe concentrate was purified by chromatography [Silica Gel, ethyl acetate:hexanes (1:1)]

Sources & evidence

ORD record
ord-18e635ac7a2e4b7e811db8c83412ef3f
Source dataset
uspto-grants-2012_05
Patent number
US08188095B2

Reaction notes

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