Methylamine → HCID 20544436, compound

HRID 2285847Notes

Reaction equation

HRID 2285847 reaction equation
[CH3:1][NH2:2].[O:3]=[C:4]1[CH:9]=[C:8]([CH3:10])O[CH:6]=[C:5]1[O:11][CH2:12][C:13]([OH:15])=[O:14]>O>[CH3:1][N:2]1[C:8]([CH3:10])=[CH:9][C:4](=[O:3])[C:5]([O:11][CH2:12][C:13]([OH:15])=[O:14])=[CH:6]1

Participants

4

Reactant 2

HCID 6329MethylamineHCID 20544472HCID 20544472, compound

Product 1

HCID 20544436HCID 20544436, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirred solution of 40% aqueous methylamine (9.0 ml) and water (9.0 ml) was added 2-(4-oxo-6-methyl-4H-pyran-3-yloxy)acetic acid (6.0 g) in small portions at room temperature. The mixture was stirred at the same temperature for 3 hours and concentrated. To the residue was added water (5 ml) and the mixture was adjusted to pH 3. The resulting precipitates were collected and washed with water to give crystals of 2-(1,6-dimethyl-4-oxo-1,4-dihydropyridin-3-yloxy)acetic acid (1.53 g), mp 240° to 242° C. The filtrate and the washings were combined together and adsorbed on Amberlite IRA-400 (Tradename, prepared by Rohm and Haas Co.) and eluted with water and then 0.3 N hydrochloric acid. The hydrochloric acid fraction was concentrated and dried to give crystals (3.7 g) of 2-(1,6-dimethyl-4-oxo-1,4-dihydropyridin-3-yloxy)acetic acid hydrochloride. The hydrochloride was dissolved in a small amount of water and the solution was adjusted to pH 3. The resulting crystals were collected by filtration and washed with water to give an additional amount of the same product (2.2 g) as obtained above.

Workup

  1. concentrationconcentrated
  2. additionTo the residue was added water (5 ml)
  3. customThe resulting precipitates
  4. customwere collected
  5. washwashed with water

Sources & evidence

ORD record
ord-0627b4df3a4f4291b289a2b11ec4e053
Source dataset
uspto-grants-1982_04
Patent number
US04324892

Reaction notes

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