Pyridine → HCID 13338838, compound

HRID 1285496Notes

Reaction equation

HRID 1285496 reaction equation
[F:1][C:2]1[C:3]([N:13]2[CH:17]=[CH:16][N:15]=[CH:14]2)=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([CH3:12])[CH:6]=[CH:5]2.N1C=CC=CC=1>C(O)(=O)C>[F:1][C:2]1[C:3]([N:13]2[CH:17]=[CH:16][N:15]=[CH:14]2)=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]([CH3:12])[CH2:6][CH2:5]2

Participants

4

Reactant 2

HCID 1049PyridineHCID 13338836HCID 13338836, compound

Product 1

HCID 13338838HCID 13338838, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 10.2 g (44.9 mmole) of 6-fluoro-5-(imidazol-1-yl)-2-methylquinoline, 16.7 g (180 mmole) of pyridine:diborane complex (that commercially available from Aldrich) and 200 ml of glacial acetic acid was stirred for about 22 hours at about 20° C. The solution was evaporated to reduce its volume, then 100 ml of 10% hydrochloric acid was added in small portions. The solution was heated on a steam bath for another one hour, then cooled with an ice bath and basified (pH 9 to 10) with 10% aqueous sodium hydroxide. The solid was separated by filtration, washed with water, and dissolved in ethyl acetate and dried. Recrystallization from aqueous ethanol provided 6-fluoro-5-(imidazol-1-yl)-1,2,3,4-tetrahydro-2-methylquinoline, m.p. 162°-164° C. Analysis: Calculated for C13H14FN3 : %C, 67.5; %H, 6.1; %N, 18.2; Found: %C, 67.5; %H, 6.1; %N, 18.0.

Workup

  1. customThe solution was evaporated
  2. addition100 ml of 10% hydrochloric acid was added in small portions
  3. temperatureThe solution was heated on a steam bath for another one hour
  4. temperaturecooled with an ice bath
  5. customThe solid was separated by filtration
  6. washwashed with water
  7. dissolutiondissolved in ethyl acetate
  8. customdried
  9. customRecrystallization from aqueous ethanol

Sources & evidence

ORD record
ord-69681928dcce433b9d2e197e016f84b3
Source dataset
uspto-grants-1986_01
Patent number
US04567269

Reaction notes

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