Hydrochloric Acid → (3-Oxo-1,2,3,4-tetrahydroquinoxalin-2-yl)acetic acid

HRID 350678Notes

Reaction equation

HRID 350678 reaction equation
[O:1]=[C:2]1[NH:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[NH:4][CH:3]1[CH2:12][C:13](N)=[O:14].Cl.[OH-:17].[Na+]>>[O:1]=[C:2]1[NH:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[NH:4][CH:3]1[CH2:12][C:13]([OH:14])=[O:17]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 2917733HCID 2917733, compound

Product 1

HCID 2783994(3-Oxo-1,2,3,4-tetrahydroquinoxalin-2-yl)acetic acid

Procedure

2-(3-Oxo-1,2,3,4-tetrahydroquinoxalin-2-yl)-acetamide (22 g, 0.11 mol) was dissolved in 10% NaOH (600 mL) and was heated under reflux for 3 hours. The mixture was cooled down via an ice-bath and was acidified with pre-cooled 10% HCl to pH -6. The solvent was concentrated and the resulting precipitate was isolated via filtration to give a gray solid as the title product: 1H NMR (DMSO-d6) δ=12.35 (bs, 1H), 10.25 (bs, 1H), 6.74–6.68 (m, 3H), 6.61–6.58 (m, 1H), 5.91 (bs, 1H), 4.08–4.04 (m, 1H), 2.69 (dd, 1H, J=5.1, 16.2 Hz), 2.51 (dd, 1H, J=6.9, 16.2 Hz)

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 3 hours
  3. temperatureThe mixture was cooled down via an ice-bath
  4. concentrationThe solvent was concentrated
  5. customthe resulting precipitate was isolated via filtration

Sources & evidence

ORD record
ord-bf6bfe7b678d4f79a9f27f66c7c772e1
Source dataset
uspto-grants-2007_02
Patent number
US07183281B2

Reaction notes

Loading…