Aniline → HCID 89782295, compound

HRID 1055996Notes

Reaction equation

HRID 1055996 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].Cl[C:11]1[CH:20]=[N:19][C:18]2[C:13](=[C:14]([Cl:21])[CH:15]=[CH:16][CH:17]=2)[N:12]=1>C1COCC1>[Cl:21][C:14]1[CH:15]=[CH:16][CH:17]=[C:18]2[C:13]=1[N:12]=[C:11]([NH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[CH:20]=[N:19]2

Participants

5

Reactant 3

HCID 6115AnilineHCID 24758Sodium hydrideHCID 106080502,8-dichloroquinoxaline

Product 1

HCID 89782295HCID 89782295, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

Aniline (0.810 ml, 8.89 mmol) was added to a mixture of NaH (60% w/w in mineral oil; 0.356 g, 8.89 mmol) in THF (59.3 ml) at 0° C.; the resulting mixture was stirred for 15 min before 2,8-dichloroquinoxaline (177a, 1.18 g, 5.93 mmol, Pharmabridge, Inc., Doylestown, Pa.) was added; the reaction mixture was stirred at 50° C. for 16 h. Purification by silica gel (100% hexanes to 40% EtOAc/hexanes) provided 8-chloro-N-phenylquinoxalin-2-amine (180a, 43% yield) as a yellow solid. MS (ESI, pos. ion) m/z: 256.2 (M+1).

Workup

  1. additionwas added
  2. customPurification by silica gel (100% hexanes to 40% EtOAc/hexanes)

Sources & evidence

ORD record
ord-643df5228df64c11bf29953b40f85768
Source dataset
uspto-grants-2016_07
Patent number
US09394297B2

Reaction notes

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