Hydrochloric Acid → HCID 12135422, compound

HRID 1270423Notes

Reaction equation

HRID 1270423 reaction equation
C[O:2][C:3](=[O:19])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[NH:10][CH2:11][C:12]1[CH:17]=[CH:16][C:15](=[O:18])[NH:14][CH:13]=1.[OH-].[Na+].Cl.C(O)C>CN(C)C=O>[O:18]=[C:15]1[NH:14][CH:13]=[C:12]([CH2:11][NH:10][C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[C:3]([OH:19])=[O:2])[CH:17]=[CH:16]1

Participants

6

Reactant 4

HCID 313Hydrochloric Acid2×HCID 702EthanolHCID 14798Sodium HydroxideHCID 69332846Methyl 2-[[(1,6-dihydro-6-oxo-3-pyridinyl)methyl]amino]benzoate

Product 1

HCID 12135422HCID 12135422, compoundYield 93.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3.5 g (12.7 mmol) of 2-[(6-oxo-1,6-dihydro-pyridin-3-ylmethyl)-amino]-benzoic acid-methyl ester is mixed in 15 ml of dimethylformamide with 30 ml of 6N sodium hydroxide solution and stirred for 1.5 hours at room temperature. While being cooled with ice, it is then mixed with about 50 ml of 4N hydrochloric acid, the precipitation is suctioned off, and it is washed with water. 3.1 g, which is taken up in 29.3 ml of 1N sodium hydroxide solution and 142 ml of ethanol, is obtained, and it is heated for 1.5 hours to a bath temperature of 120° C. The ethanol is then drawn off in a vacuum, it is made acidic with 2N hydrochloric acid, and the precipitated product is suctioned off and dried well. 2.9 g (93.5% of theory) of 2-[(6-oxo-1,6-dihydro-pyridin-3-ylmethyl)-amino]-benzoic acid is obtained.

Workup

  1. temperatureWhile being cooled with ice, it
  2. customthe precipitation
  3. washit is washed with water
  4. custom142 ml of ethanol, is obtained
  5. temperatureit is heated for 1.5 hours to a bath temperature of 120° C
  6. customdried well

Sources & evidence

ORD record
ord-f9aa669250444c43959db2da3d1a7156
Source dataset
uspto-grants-2007_04
Patent number
US07202260B2

Reaction notes

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