Dimethylformamide → HCID 20544451, compound

HRID 426986Notes

Reaction equation

HRID 426986 reaction equation
[O:1]=[C:2]1[CH:7]=[C:6]([CH2:8]O)[NH:5][CH:4]=[C:3]1[O:10][CH2:11][C:12]([OH:14])=[O:13].S(Cl)([Cl:17])=O.CN(C)C=O.C(=O)(O)[O-].[Na+]>O>[O:1]=[C:2]1[CH:7]=[C:6]([CH2:8][Cl:17])[NH:5][CH:4]=[C:3]1[O:10][CH2:11][C:12]([OH:14])=[O:13]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 516892Sodium BicarbonateHCID 20544454HCID 20544454, compound

Product 1

HCID 20544451HCID 20544451, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To crystals (10 g) of 2 -(4-oxo-6-hydroxymethyl-1,4-dihydropyridin-3-yloxy)acetic acid was added thionyl chloride (25 ml), and the mixture was stirred for 30 minutes. After cooling, dimethylformamide (125 ml) was added to the reaction mixture, and the resultant mixture was stirred for an hour. The resultant mixture was poured into cold water (750 ml) and the aqueous solution was adjusted to pH 3 with an aqueous sodium bicarbonate solution and then cooled with ice for 2 hours. Precipitated crystals were collected by filtration and washed with water to give crystals (8.7 g) of 2-(4-oxo-6-chloromethyl-1,4-dihydropyridin-3-yloxy)acetic acid. (This product was converted to its hydrochloride monohydrate, m.p. 150° to 155° C. by recrystallizing from a mixture of 10% hydrochloric acid (5 ml) and water (5 ml).)

Workup

  1. temperatureAfter cooling
  2. temperaturecooled with ice for 2 hours
  3. customPrecipitated crystals
  4. filtrationwere collected by filtration
  5. washwashed with water

Sources & evidence

ORD record
ord-22b7c08ffcce4606b8e6ebcd76a3d40a
Source dataset
uspto-grants-1979_10
Patent number
US04172198

Reaction notes

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