Diethyl Ether → HCID 178518268, compound

HRID 2236595Notes

Reaction equation

HRID 2236595 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[NH:7][C:6](=[O:13])/[C:5]/2=[CH:14]/OC.[NH2:17][CH2:18][C:19]1[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=1.C(OCC)C>CN(C=O)C>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[NH:7][C:6](=[O:13])/[C:5]/2=[CH:14]\[NH:17][CH2:18][C:19]1[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 310183-PyridinemethanamineHCID 68692760(E)-6-bromo-4-(methoxymethylene)isoquinoline-1,3(2H,4H)-dione

Product 1

HCID 178518268HCID 178518268, compoundYield 63.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of (4E)-6-bromo-4-(methoxymethylene)isoquinoline-1,3(2H,4H)-dione (0.2 g, 0.71 mmol) in N,N′-dimethylformamide is added 3-(aminomethyl)pyridine (0.073 mL, 0.71 mmol). The reaction mixture is heated at 60° C. under N2. After reaction is completed, diethyl ether is added, and the red precipitate is isolated and washed with methanol, ether, and hexane respectively to afford 0.16 g (63.2% yield) of orange solid: mp 299-300° C.; 1H NMR (DMSO-d6) δ 11.09 (s, 1H), 10.69 (m, 1H), 8.74 (d, J=9 Hz, 1H), 8.63 (s, 1H), 8.52 (d, J=3 Hz, 1H), 8.10 (s, 1H), 7.84 (m, 2H), 7.42 (m, 1H), 7.31 (d, J=9 Hz, 1H), 3.40 (d, J=4.8 Hz, 2H); MS (ESI) m/z 355.7 and 357.7 (M−H)−1, Analysis for C16H12BrN3O2, Calcd: C, 53.70; H, 3.38; N, 11.70. Found: C, 53.45; H, 3.23; N, 11.74.

Workup

  1. customAfter reaction
  2. customthe red precipitate is isolated
  3. washwashed with methanol, ether, and hexane respectively

Sources & evidence

ORD record
ord-29aa4e34a0a0475b97e9dabe253e2057
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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