Benzylamine → HCID 9970137, compound

HRID 1282301Notes

Reaction equation

HRID 1282301 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.[CH2:22]([NH2:29])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>>[CH2:22]([NH:29][C:15]([C:9]1[C:10]2[N:11]=[C:12]([O:13][CH3:14])[C:3]([O:2][CH3:1])=[N:4][C:5]=2[CH:6]=[C:7]([N+:19]([O-:21])=[O:20])[C:8]=1[CH3:18])=[O:16])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

3

Reactant 2

HCID 7504BenzylamineHCID 10805016HCID 10805016, compound

Product 1

HCID 9970137HCID 9970137, compound

Procedure

Prepared from 2,3-dimethoxy-6-methyl-7-nitro-quinoxaline-5-carbonyl chloride (13) 250 mg (0.80 mmol) and benzylamine 90 μL (0.84 mmol). Reaction was continued for 24 hours, and the crude product was eluted through a flash column (7:3 hexanes:ethyl acetate), 260 mg (84%), mp 171-173° C.; 1H NMR (CCl3): δ 8.32 (s, 1H), 7.32 (m, 5H), 6.12 (br s, 1H), 4.68 (d, 2H, J=5.6 Hz), 4.06 (s, 3H), 3.92 (s, 3H), 2.56 (s, 3H); MS (APCI): m/z 383 (M+1). Anal Calcd. for C19H18N4O5: C, 59.68; H, 4.74; N, 14.65. Found: C, 59.63; H, 4.94; N, 14.56.

Workup

  1. customReaction
  2. washthe crude product was eluted through a flash column (7:3 hexanes:ethyl acetate), 260 mg (84%), mp 171-173° C.

Sources & evidence

ORD record
ord-40d94ec89d7e4ed8bc10b631caecafae
Source dataset
uspto-grants-2002_09
Patent number
US06455698B1

Reaction notes

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