Hydrochloric Acid → HCID 178516746, compound

HRID 1821773Notes

Reaction equation

HRID 1821773 reaction equation
Cl.[NH2:2][CH2:3][C:4]([NH2:6])=[O:5].[OH-].[Na+].[C:9]1([C:15]([C:17]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=O)=O)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.Cl>CO>[OH:5][C:4]1[CH:3]=[N:2][C:17]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[C:15]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[N:6]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8651BenzilHCID 14798Sodium HydroxideHCID 2723639Glycinamide hydrochloride

Product 1

HCID 178516746HCID 178516746, compoundYield 80.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Conditions

Temperature
0 °C

Procedure

To a stirred suspension of glycinamide hydrochloride (1.1 gm, 10 mmol) in 20 mL MeOH at 0° C. was added 20% NaOH (10 mL, 50 mmol). A clear solution formed and was treated slowly portionwise with benzil (2.1 gm, 10 mmol) as a solid. The yellow solution was stirred at 0° C. for 2 hours and then neutralized to approximately pH=7 with concentrated HCl. The bright yellow color disappeared and a tan precipitate formed. The material was isolated by filtration with MeOH and triturated with EtOAc to give 2-hydroxy-5,6-diphenylpyrazine (2 gm, 80%). 1H-NMR (400 MHz, CDCl3) δ 8.24 (s, 1H), 7.42-7.31 (m, 4H), 7.39-7.21 (m, 6H).

Workup

  1. customA clear solution formed
  2. customa tan precipitate formed
  3. customtriturated with EtOAc

Sources & evidence

ORD record
ord-62d491a2e4d940999e32699780cdc93b
Source dataset
uspto-grants-2009_10
Patent number
US07608618B2

Reaction notes

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