P-Anisidine → HCID 10111456, compound

HRID 1251017Notes

Reaction equation

HRID 1251017 reaction equation
[CH3:1][O:2][C:3]1[C:12]([O:13][CH3:14])=[N:11][C:10]2[C:9]([C:15](Cl)=[O:16])=[C:8]([CH3:18])[C:7]([N+:19]([O-:21])=[O:20])=[CH:6][C:5]=2[N:4]=1.[CH3:22][O:23][C:24]1[CH:29]=[CH:28][C:27]([NH2:30])=[CH:26][CH:25]=1>>[CH3:22][O:23][C:24]1[CH:29]=[CH:28][C:27]([NH:30][C:15]([C:9]2[C:10]3[N:11]=[C:12]([O:13][CH3:14])[C:3]([O:2][CH3:1])=[N:4][C:5]=3[CH:6]=[C:7]([N+:19]([O-:21])=[O:20])[C:8]=2[CH3:18])=[O:16])=[CH:26][CH:25]=1

Participants

3

Reactant 2

HCID 7732P-AnisidineHCID 10805016HCID 10805016, compound

Product 1

HCID 10111456HCID 10111456, compound

Procedure

Prepared from 2,3-dimethoxy-6-methyl-7-nitro-quinoxaline-5-carbonyl chloride (13) 250 mg (0.80 mmol) and 4-anisidine 207 mg (1.68 mmol). Reaction was continued for 24 hours, and the crude product was eluted through a flash column (3:2 hexanes:ethyl acetate), 210 mg (66%), mp 206-208° C.; 1H NMR (CDCl3): δ 8.33 (s, 1H), 7.71 (d, 2H, J=9.0 Hz), 7.60 (s, 1H), 6.88 (d, 2H, J=8.8 Hz), 4.16 (s, 3H), 4.00 (s, 3H), 3.79 (s, 3H), 2.57 (s, 3H); MS (APCI): m/z 399 (M+H).

Workup

  1. customReaction
  2. washthe crude product was eluted through a flash column (3:2 hexanes:ethyl acetate), 210 mg (66%), mp 206-208° C.

Sources & evidence

ORD record
ord-3788578b25be4f1893691187fa35135c
Source dataset
uspto-grants-2002_01
Patent number
US06340758B1

Reaction notes

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