Bromine → HCID 13464026, compound

HRID 903892Notes

Reaction equation

HRID 903892 reaction equation
[Br:1]Br.[CH:3]1[C:8]2[C:9](=[O:18])[C:10]3[CH:17]=[CH:16][CH:15]=[CH:14][C:11]=3[CH:12]=[CH:13][C:7]=2[CH:6]=[CH:5][N:4]=1>C(O)(=O)C>[Br:1][C:13]1[C:7]2[CH:6]=[CH:5][N:4]=[CH:3][C:8]=2[C:9](=[O:18])[C:10]2[CH:17]=[CH:16][CH:15]=[CH:14][C:11]=2[CH:12]=1

Participants

4

Reactant 2

HCID 24408BromineHCID 12792398HCID 12792398, compound

Product 1

HCID 13464026HCID 13464026, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

Bromine (4.18 ml.) in acetic acid (50 ml.) is added dropwise to a stirred solution of benzo[5,6]cyclohepta[1,2-c]pyridin-11-one (12.35 g.) in acetic acid (250 ml.). The resulting mixture is heated on the steam bath for 24 hours and the acetic acid is removed under reduced pressure. Saturated Na2CO3 solution (500 ml.) is added to the residue and the deep yellow solid that forms is collected, washed with water, and dried. This crude product is recrystallized from 1-chlorobutane to give 9.3 g., m.p. 167°-169° C.

Workup

  1. temperatureThe resulting mixture is heated on the steam bath for 24 hours
  2. customthe acetic acid is removed under reduced pressure
  3. additionSaturated Na2CO3 solution (500 ml.) is added to the residue
  4. customthe deep yellow solid that forms is collected
  5. washwashed with water
  6. customdried
  7. customThis crude product is recrystallized from 1-chlorobutane
  8. customto give 9.3 g

Sources & evidence

ORD record
ord-79a660efc79e45e2a2593a00902c9691
Source dataset
uspto-grants-1980_10
Patent number
US04229455

Reaction notes

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