Sodium Carbonate → 2-Hydroxy-N-[5-(1-methyl-2-oxo-1,2,3,4-tetrahydro-quinolin-6-yl)-pyridin-3-yl]-acetamide

HRID 1774785Notes

Reaction equation

HRID 1774785 reaction equation
[CH3:1][N:2]1[C:11]2[C:6](=[CH:7][C:8]([C:12]3[CH:13]=[C:14]([NH:18][C:19]([CH2:21][O:22]C(=O)C)=[O:20])[CH:15]=[N:16][CH:17]=3)=[CH:9][CH:10]=2)[CH2:5][CH2:4][C:3]1=[O:26].C([O-])([O-])=O.[Na+].[Na+]>CO>[OH:22][CH2:21][C:19]([NH:18][C:14]1[CH:15]=[N:16][CH:17]=[C:12]([C:8]2[CH:7]=[C:6]3[C:11](=[CH:10][CH:9]=2)[N:2]([CH3:1])[C:3](=[O:26])[CH2:4][CH2:5]3)[CH:13]=1)=[O:20]

Participants

4

Reactant 2

HCID 10340Sodium CarbonateHCID 71533146Acetic acid [5-(1-methyl-2-oxo-1,2,3,4-tetrahydro-quinolin-6-yl)-pyridin-3-ylcarbamoyl]-methyl ester

Product 1

HCID 715331982-Hydroxy-N-[5-(1-methyl-2-oxo-1,2,3,4-tetrahydro-quinolin-6-yl)-pyridin-3-yl]-acetamideYield 91%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of acetic acid [5-(1-methyl-2-oxo-1,2,3,4-tetrahydro-quinolin-6-yl)-pyridin-3-ylcarbamoyl]-methyl ester (example 2, 0.025 g, 0.071 mmol) in MeOH (1 mL) was added a 1M aqueous solution of Na2CO3 (0.354 mL) and the reaction mixture was stirred at room temperature for 1 h. The mixture was evaporated to dryness, the residue dissolved in EtOAc (20 mL) and washed with aq. NaHCO3 (5 mL). The organic layer was separated, dried over Na2SO4, filtered and evaporated to dryness to give the title compound (0.02 g, 91%) as light brown solid. MS: 312.1 (M+H+).

Workup

  1. customThe mixture was evaporated to dryness
  2. dissolutionthe residue dissolved in EtOAc (20 mL)
  3. washwashed with aq. NaHCO3 (5 mL)
  4. customThe organic layer was separated
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. customevaporated to dryness

Sources & evidence

ORD record
ord-0e25e6bb1de44a0bbb8687d3703e8c37
Source dataset
uspto-grants-2016_02
Patent number
US09260408B2

Reaction notes

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