Cyclopropylamine → 3-Benzyloxy-1-cyclopropyl-6-methyl-4-oxo-1,4-dihydro-pyridine-2-carboxylic acid

HRID 1367660Notes

Reaction equation

HRID 1367660 reaction equation
[CH2:1]([O:8][C:9]1[C:14](=[O:15])[CH:13]=[C:12]([CH3:16])O[C:10]=1[C:17]([OH:19])=[O:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:20]1([NH2:23])[CH2:22][CH2:21]1>O>[CH2:1]([O:8][C:9]1[C:14](=[O:15])[CH:13]=[C:12]([CH3:16])[N:23]([CH:20]2[CH2:22][CH2:21]2)[C:10]=1[C:17]([OH:19])=[O:18])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 69828CyclopropylamineHCID 98564973-(benzyloxy)-6-methyl-4-oxo-4H-pyran-2-carboxylic acid

Product 1

HCID 666589263-Benzyloxy-1-cyclopropyl-6-methyl-4-oxo-1,4-dihydro-pyridine-2-carboxylic acidYield 93%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a suspension of 3-(benzyloxy)-6-methyl-4-oxo-4H-pyran-2-carboxylic acid (2.0 g, 7.685 mmol) in H2O (10 ml) in a reaction tube with a stirrer, was added cyclopropylamine (2.13 ml, 30.74 mmol). A clear light yellow solution was formed. The reaction mixture was heated for ca. 19 h in a sealed tube. The reaction mixture then worked up as described in Procedure II. Thus, the title compound (2.14 g, 93%) was obtained as an off white solid.

Workup

  1. customA clear light yellow solution was formed
  2. temperatureThe reaction mixture was heated for ca. 19 h in a sealed tube

Sources & evidence

ORD record
ord-3109bd0d69bd45c8b06ccab59da5a162
Source dataset
uspto-grants-2011_02
Patent number
US07893269B2

Reaction notes

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