Tetrahydrofuran → (3-Amino-6-chloro-2-pyrazinyl)phenylmethanone

HRID 1075770Notes

Reaction equation

HRID 1075770 reaction equation
[NH2:1][C:2]1[C:7]([C:8](N2CCCC2)=[O:9])=[N:6][C:5]([Cl:15])=[CH:4][N:3]=1.[C:16]1([Mg]Br)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.O1CCCC1>O>[NH2:1][C:2]1[C:7]([C:8](=[O:9])[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[N:6][C:5]([Cl:15])=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 54164581HCID 54164581, compoundHCID 178418255HCID 178418255, compound

Product 1

HCID 21541161(3-Amino-6-chloro-2-pyrazinyl)phenylmethanone

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2-Amino-5-chloropyrazine-3-carboxylic acid pyrrolidide (9 g. or 0.04 mol) was added to a freshly prepared solution of 36.2 g. (0.2 mol) of phenylmagnesium bromide in 300 ml. of tetrahydrofuran cooled to 20°. After addition, the reaction mixture was stirred for 3 hours at room temperature and was then hydrolyzed by addition of 150 ml. of water. The organic layer was separated, dried over alumina, filtered and evaporated. Crystallization of the oil obtained from ether yielded 2 g. (50%) of the above-named product as yellow crystals, m.p. 158°-161°. The analytical sample was recrystallized from ethyl acetate, m.p. 160°-161°.

Workup

  1. additionAfter addition
  2. additionwas then hydrolyzed by addition of 150 ml
  3. customThe organic layer was separated
  4. customdried over alumina
  5. filtrationfiltered
  6. customevaporated
  7. customCrystallization of the oil
  8. customobtained from ether
  9. customyielded 2 g
  10. customThe analytical sample was recrystallized from ethyl acetate, m.p. 160°-161°

Sources & evidence

ORD record
ord-8d762fbff8ab4465b71532d818ca289b
Source dataset
uspto-grants-1976_05
Patent number
US03954753

Reaction notes

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