Hydrochloric Acid → HCID 13567760, compound

HRID 280190Notes

Reaction equation

HRID 280190 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:10]=O)[C:5]([O:8][CH3:9])=[N:6][CH:7]=1.[CH3:12][C:13]([C:15]1[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=1)=[O:14].[OH-].[K+].Cl>O1CCCC1.O.CO>[Br:1][C:2]1[CH:3]=[C:4](/[CH:10]=[CH:12]/[C:13]([C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=2)=[O:14])[C:5]([O:8][CH3:9])=[N:6][CH:7]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 7467P-ChloroacetophenoneHCID 14797Potassium HydroxideHCID 15164035-Bromo-2-methoxypyridine-3-carbaldehyde

Product 1

HCID 13567760HCID 13567760, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 6.5 g of 5-bromo-2-methoxypyridine-3-carboxaldehyde in 30 ml of tetrahydrofuran under nitrogen was added 200 ml of methanol followed by 4.6 g of 4-chloroacetophenone. Then, a solution of 6.6 g of 85% potassium hydroxide in 15 ml of water was added. The mixture warmed, became yellow, and deposited a thick precipitate. It was then stirred mechanically for about 1.5 hours until the temperature fell back to about 25° C. It was then further cooled in an ice bath and neutralized by the addition of 20 ml of aqueous 5M hydrochloric aid in small portions. The resulting pasty mixture was poured into 400 ml of water, acidified to a pH of 1 with aqueous 1N hydrochloric acid and then filtered. The moist product was boiled with 2-propanol/ethyl acetate (3:1), cooled and filtered. The filter cake was dried under reduced pressure to give (E)-3-(5-bromo-2-methoxy-3-pyridinyl)-1-(4-chlorophenyl)-2-propen-1-one as a pale yellow solid melting at about 168.5°-171.5° C.

Workup

  1. temperatureThe mixture warmed
  2. customfell back to about 25° C
  3. temperatureIt was then further cooled in an ice bath
  4. additionneutralized by the addition of 20 ml of aqueous 5M hydrochloric aid in small portions
  5. filtrationfiltered
  6. temperaturecooled
  7. filtrationfiltered
  8. customThe filter cake was dried under reduced pressure

Sources & evidence

ORD record
ord-010e0abf979045488bd683666ec0d9a5
Source dataset
uspto-grants-1986_05
Patent number
US04588733

Reaction notes

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