Hydrochloric Acid → 2-(Quinolin-6-yl)propanoic acid

HRID 219139Notes

Reaction equation

HRID 219139 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][C:7]([CH:11]([CH3:16])[C:12]([O:14]C)=[O:13])=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.CO.[OH-].[Na+].Cl>>[N:1]1[C:10]2[C:5](=[CH:6][C:7]([CH:11]([CH3:16])[C:12]([OH:14])=[O:13])=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14798Sodium HydroxideHCID 57691200Methyl 2-(quinolin-6-YL)propanoate

Product 1

HCID 190360062-(Quinolin-6-yl)propanoic acidYield 77%

Conditions

Temperature
25 °C

Procedure

To a 15 ml round-bottomed flask was added methyl 2-(quinolin-6-yl)propanoate (1.0 g, 4.7 mmol), methanol (5.0 ml, 12 mmol) and aq. sodium hydroxide (5 M, 2.3 ml, 12 mmol). The mixture was stirred at 25° C. for 24 h. The mixture was neutralized with aq. HCl (5 M, 2.3 mL, 12 mmol). After sitting overnight a white precipitate had formed. The mixture was filtered and the filtercake was washed with water and then dried in vacuo to afford the title compound as a white solid (0.72 g, 77%). MS (ESI, pos. ion) m/z: 202 (M+1).

Workup

  1. waitAfter sitting overnight
  2. customa white precipitate had formed
  3. filtrationThe mixture was filtered
  4. washthe filtercake was washed with water
  5. customdried in vacuo

Sources & evidence

ORD record
ord-86bebdd259ff4ef7ada8f9265af8f07b
Source dataset
uspto-grants-2012_06
Patent number
US08198448B2

Reaction notes

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