Hydrochloric Acid → HCID 23352069, compound

HRID 1708147Notes

Reaction equation

HRID 1708147 reaction equation
[O:1]=[C:2]1[NH:10][C:9]([CH2:11][CH2:12][CH3:13])=[CH:8][C:4]([C:5](O)=[O:6])=[CH:3]1.Cl.O>C1COCC1>[OH:6][CH2:5][C:4]1[CH:8]=[C:9]([CH2:11][CH2:12][CH3:13])[NH:10][C:2](=[O:1])[CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 125867772-Oxo-6-propyl-1,2-dihydropyridine-4-carboxylic acid

Product 1

HCID 23352069HCID 23352069, compoundYield 46.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

27.8 ml and, after 1 hour at room temperature, a further 27.8 ml of a 1M solution of BH3 in THF are added dropwise at 0° C. to a suspension of 3.0 g (16.6 mmol) of 2-oxo-6-propyl-1,2-dihydroisonicotinic acid and the mixture is stirred for a further hour at room temperature. 66.8 ml of 1N hydrochloric acid and 100 ml of water are added to the now clear solution, and it is stirred at room temperature for 1 hour and extracted three times with 75 ml of ethyl acetate each time. The organic phase is discarded, the aqueous phase is adjusted to a pH of about 7 with satd. NaHCO3 solution and the deposited precipitate is filtered off with suction. The aqueous filtrate is concentrated to dryness in a rotary evaporator and recrystallised from about 80 ml of water together with the first precipitate. 1.28 g (46%) of colourless crystals of m.p. 167° C. are obtained.

Workup

  1. stirringis stirred at room temperature for 1 hour
  2. extractionextracted three times with 75 ml of ethyl acetate each time
  3. filtrationNaHCO3 solution and the deposited precipitate is filtered off with suction
  4. concentrationThe aqueous filtrate is concentrated to dryness in a rotary evaporator
  5. customrecrystallised from about 80 ml of water together with the first precipitate

Sources & evidence

ORD record
ord-b76ecdfeeefd46b5b934646928715054
Source dataset
uspto-grants-1994_10
Patent number
US05356911

Reaction notes

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