2-Bromopyridine → HCID 21533540, compound

HRID 1657488Notes

Reaction equation

HRID 1657488 reaction equation
[CH2:1]([O:8][C:9]1[CH:15]=[CH:14][C:12]([NH2:13])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=1>>[N:18]1[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=1[NH:13][C:12]1[CH:11]=[CH:10][C:9]([O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[CH:15][CH:14]=1

Participants

3

Reactant 2

HCID 79732-BromopyridineHCID 228604-Benzyloxyaniline

Product 1

HCID 21533540HCID 21533540, compound

Procedure

A mixture of 19.93 g. of 4-benzyloxyaniline and 4.77 ml. of 2-bromopyridine was stirred and gradually heated over a period of 21/2 hours to 150°C. The mixture was held at 160°C. for 1 hour and at 130°C. for one and three-quarters hours, and then steam distilled. The residue was filtered and the filtrate made alkaline. The combined solid products were recrystallized from cyclohexane to give N-(2-pyridyl)-4-benzyloxyaniline, tan prisms, m.p. 110°-111.5°C.

Workup

  1. additionA mixture of 19.93 g
  2. distillationsteam distilled
  3. filtrationThe residue was filtered
  4. customThe combined solid products were recrystallized from cyclohexane

Sources & evidence

ORD record
ord-c931752eee2e414eb874a0dd295d9b31
Source dataset
uspto-grants-1976_06
Patent number
US03960886

Reaction notes

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