Aniline → HCID 89782082, compound

HRID 1056002

Reaction equation

HRID 1056002 reaction equation
[Li+].C[Si]([N-][Si](C)(C)C)(C)C.[Br:11][C:12]1[CH:21]=[CH:20][CH:19]=[C:18]2[C:13]=1[N:14]=[C:15](Cl)[C:16]([CH3:22])=[N:17]2.[NH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>O1CCOCC1.CCOC(C)=O>[Br:11][C:12]1[CH:21]=[CH:20][CH:19]=[C:18]2[C:13]=1[N:14]=[C:15]([NH:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:16]([CH3:22])=[N:17]2

Participants

6

Reactant 3

HCID 6115AnilineHCID 2733832Lithium HexamethyldisilazideHCID 894288875-Bromo-3-chloro-2-methylquinoxaline

Product 1

HCID 89782082HCID 89782082, compoundYield 71%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

LHMDS (1.0M in THF; 14.37 ml, 14.37 mmol) was added to a solution of 5-bromo-3-chloro-2-methylquinoxaline (126e, 0.74 g, 2.87 mmol) and aniline (1.309 ml, 14.37 mmol, Alfa Aesar, Ward Hill, Mass.) in dioxane (28.7 ml) at RT, and the resulting mixture was stirred at RT for 30 min. The mixture was diluted with EtOAc (200 ml), added to a separatory funnel, and washed with saturated aq. NH4Cl (2×150 ml) before the organic layer was separated, dried over Na2SO4, and concentrated. Purification by silica gel (100% hexanes to 20% EtOAc/hexanes) provided 8-bromo-3-methyl-N-phenylquinoxalin-2-amine (183a, 71% yield) as a brown oil. MS (ESI, pos. ion) m/z: 314.2/316.2 (M+1).

Workup

  1. additionadded to a separatory funnel
  2. washwashed with saturated aq. NH4Cl (2×150 ml) before the organic layer
  3. customwas separated
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customPurification by silica gel (100% hexanes to 20% EtOAc/hexanes)

Sources & evidence

ORD record
ord-2e342e456a10458b950e04da86d5375f
Source dataset
uspto-grants-2016_07
Patent number
US09394297B2

Linked notes

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