Hydrogen Bromide → 5-(4-Aminophenyl)-2(1H)-pyrazinone hydrobromide

HRID 542467Notes

Reaction equation

HRID 542467 reaction equation
C(OC([NH:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[N:19]=[CH:20][C:21](=[O:24])[NH:22][CH:23]=2)=[CH:14][CH:13]=1)=O)C1C=CC=CC=1.[BrH:25]>C(O)(=O)C>[BrH:25].[NH2:11][C:12]1[CH:13]=[CH:14][C:15]([C:18]2[N:19]=[CH:20][C:21](=[O:24])[NH:22][CH:23]=2)=[CH:16][CH:17]=1

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 12358023Benzyl 4-(5-hydroxypyrazin-2-yl)phenylcarbamate

Product 1

HCID 202086625-(4-Aminophenyl)-2(1H)-pyrazinone hydrobromide

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 5-(4-benzyloxycarbonylaminophenyl)-2(1H)-pyrazinone (1.1 g) in 15% w/v hydrogen bromide in acetic acid solution (30 ml) was refluxed for 30 min. The yellow precipitate which formed was filtered off and it was washed with a little 1-propanol and then recrystallised from ethanol-water containing 2 drops of concentrated hydrobromic acid to give 5-(4-aminophenyl)-2(1H)-pyrazinone hydrobromide (1.03 m.p. >300° C.).

Workup

  1. temperaturewas refluxed for 30 min
  2. customThe yellow precipitate which formed
  3. filtrationwas filtered off
  4. washit was washed with a little 1-propanol
  5. customrecrystallised from ethanol-water containing 2 drops of concentrated hydrobromic acid

Sources & evidence

ORD record
ord-c4ad039f06124355beb7590d805249bc
Source dataset
uspto-grants-1987_04
Patent number
US04657906

Reaction notes

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