Tetrahydrofuran → 3-Amino-6-chloro-2-valeramidoquinoxaline

HRID 1288224Notes

Reaction equation

HRID 1288224 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([NH:12][C:13](=[O:18])[CH2:14][CH2:15][CH2:16][CH3:17])[C:6]([NH:19]C(=O)CCCC)=[N:5]2.N1CCCC1.O1CCCC1>O>[NH2:19][C:6]1[C:7]([NH:12][C:13](=[O:18])[CH2:14][CH2:15][CH2:16][CH3:17])=[N:8][C:9]2[C:4]([N:5]=1)=[CH:3][C:2]([Cl:1])=[CH:11][CH:10]=2

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 31268PyrrolidineHCID 215045946-Chloro-2,3-bis-(valeramido)quinoxaline

Product 1

HCID 215045893-Amino-6-chloro-2-valeramidoquinoxaline

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 12 parts of 6-chloro-2,3 bis(valeramido)quinoxaline and 2.5 parts of pyrrolidine in 220 parts of tetrahydrofuran was permitted to stand at ambient temperature for seven days. The solution was then poured into 750 parts of water and the solid which separated was removed by filtration and washed with water, pressed dry, and washed with hexane. The crude product was dissolved in 108 parts of boiling ethyl acetate and the resulting solution filtered. Upon addition of 100 parts of hexane and subsequent cooling, the solution deposited 3 parts of 3-amino-6-chloro-2-valeramidoquinoxaline as a pale yellow solid, m.p. 224°-228° C.

Workup

  1. customthe solid which separated
  2. customwas removed by filtration
  3. washwashed with water
  4. custompressed dry
  5. washwashed with hexane
  6. dissolutionThe crude product was dissolved in 108 parts of boiling ethyl acetate
  7. filtrationthe resulting solution filtered
  8. additionUpon addition of 100 parts of hexane and subsequent cooling

Sources & evidence

ORD record
ord-98b54217f6e54267959204cd1fc63b95
Source dataset
uspto-grants-1976_10
Patent number
US03987171

Reaction notes

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