Benzyl Alcohol → 6-(Benzyloxy)pyrazine-2-carboxylic acid

HRID 2294924Notes

Reaction equation

HRID 2294924 reaction equation
[CH2:1]([OH:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].Cl[C:12]1[N:17]=[C:16]([C:18]([OH:20])=[O:19])[CH:15]=[N:14][CH:13]=1.Cl>>[CH2:1]([O:8][C:12]1[N:17]=[C:16]([C:18]([OH:20])=[O:19])[CH:15]=[N:14][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 4

HCID 244Benzyl AlcoholHCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 145008756-Chloropyrazine-2-carboxylic acid

Product 1

HCID 214715936-(Benzyloxy)pyrazine-2-carboxylic acid

Procedure

To 1 mL of benzyl alcohol cooled in an ice bath was added 0.1 g of 60% sodium hydride oil dispersion. After 15 min., 0.1 g of 6-chloro-2-pyrazinoic acid was added. The mixture was stirred at room temperature for 1 h, then acidified with 2 mL of 1N HCl. The mixture was cooled in an ice bath and the white precipitate collected by filtration. Drying under vacuum gave 0.132 g of 6-benzyloxy-2-pyrazinoic acid: mp 160°-162° C.; 1H NMR (400 MHz, CDCl3) 9.00 (s, 1H), 8.56 (s, 1H), 7.49-7.36 (m, 5H), 5.46 (s, 2H).

Workup

  1. temperatureThe mixture was cooled in an ice bath
  2. filtrationthe white precipitate collected by filtration
  3. customDrying under vacuum

Sources & evidence

ORD record
ord-47bdcd5573b84705b73945cff37e1ce6
Source dataset
uspto-grants-1997_11
Patent number
US05691323

Reaction notes

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