HCID 13464026, compound → HCID 13464027, compound

HRID 903893Notes

Reaction equation

HRID 903893 reaction equation
[CH3:1][Mg]Br.[Br:4][C:5]1[C:15]2[CH:14]=[CH:13][N:12]=[CH:11][C:10]=2[C:9](=[O:16])[C:8]2[CH:17]=[CH:18][CH:19]=[CH:20][C:7]=2[CH:6]=1>C1COCC1>[Br:4][C:5]1[C:15]2[CH:14]=[CH:13][N:12]=[CH:11][C:10]=2[C:9]([CH3:1])([OH:16])[C:8]2[CH:17]=[CH:18][CH:19]=[CH:20][C:7]=2[CH:6]=1

Participants

4

Reactant 2

HCID 13464026HCID 13464026, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 13464027HCID 13464027, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methyl magnesium bromide (27.6 ml., 2.9 M in ether) is added dropwise to a solution of 5-bromobenzo[5,6]cyclohepta[1,2-c]pyridin-11-one (20.02 g., 0.07 mol) in dry THF (300 ml.) with cooling. When addition is complete, the cooling bath is removed and the mixture is stirred for 20-24 hours. The solvent is removed in vacuo, the residue is taken up in water (300 ml.) and acidified by the addition of acetic acid. The solid that forms is collected, washed with water then recrystallized from 2-propanol to give 16.25 g., m.p. 226.5°-229.5° C.

Workup

  1. temperaturewith cooling
  2. additionWhen addition
  3. customthe cooling bath is removed
  4. customThe solvent is removed in vacuo
  5. additionacidified by the addition of acetic acid
  6. customThe solid that forms is collected
  7. washwashed with water
  8. customthen recrystallized from 2-propanol
  9. customto give 16.25 g

Sources & evidence

ORD record
ord-f545cd64b8db4de2a51f2ec27fc2c374
Source dataset
uspto-grants-1980_10
Patent number
US04229455

Reaction notes

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