Dimethylformamide → HCID 23042541, compound

HRID 2165880Notes

Reaction equation

HRID 2165880 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([CH3:12])[CH:10]=2)[CH:5]=[C:4]([C:13]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[CH:16]=[CH:15][CH:14]=2)[N:3]=1.[CH3:23][N:24]([CH3:29])[CH:25](NC)[CH3:26].C(=O)([O-])[O-].[K+].[K+].[CH3:36][N:37](C=O)C>O>[CH3:29][N:24]([CH3:23])[CH2:25][CH2:26][N:37]([CH3:36])[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([CH3:12])[CH:10]=2)[CH:5]=[C:4]([C:13]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[CH:16]=[CH:15][CH:14]=2)[N:3]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 11062323HCID 11062323, compoundHCID 14839240HCID 14839240, compound

Product 1

HCID 23042541HCID 23042541, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of the product of Example 31, Part A, 1-chloro-7-methyl-3-(1-naphthalenyl)-isoquinoline (2.00 g, 6.58 mmol), N,N,N'-trimethylethanediamine (1.7 mL, 13.4 mmol), and potassium carbonate (2.75 g, 19.9 mmol) in DMF (5 mL) was refluxed overnight. The reaction mixture was cooled to room temperature, diluted with water, and extracted with methylene chloride. The combined organic extracts were washed with water, dried, and concentrated. The residue was purified by flash chromatography with 1:1 hexane-ethyl acetate to afford the title compound (2.08 g, 5.63 mmol, 86% yield) as an oil: IR(CHCl3) 3052, 1591 cm-1 ; MS m/e 370(M+ +H); 1H NMR(CDCl3) δ 8.23-8.37(m,1H), 8.03(s,1H), 7.80-7.97(m,2H), 7.63-7.79(m,2H), 7.33-7.62(m,5H), 3.62(t,J=7 Hz,2H), 3.13(s,3H), 2.80(t,J=7 Hz,2H), 2.60(s,3H), 2.30(s,6H).

Workup

  1. temperaturewas refluxed overnight
  2. extractionextracted with methylene chloride
  3. washThe combined organic extracts were washed with water
  4. customdried
  5. concentrationconcentrated
  6. customThe residue was purified by flash chromatography with 1:1 hexane-ethyl acetate

Sources & evidence

ORD record
ord-b629ce11ba6f49c4bea3aac03b4dbc9d
Source dataset
uspto-grants-1990_07
Patent number
US04942163

Reaction notes

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