Dimethylformamide → HCID 14366447, compound

HRID 582639Notes

Reaction equation

HRID 582639 reaction equation
[CH:1]1[C:17]2[C:16]([C:18]([OH:20])=[O:19])=C3[C:7](=[C:8]4C(=N3)[CH:12]=[CH:11][CH:10]=[CH:9]4)[NH:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.[OH-].[K+].[CH3:23]I.[CH3:25][N:26]([CH:28]=O)[CH3:27]>>[CH3:27][N:26]1[C:25]2[C:16]([C:18]([O:20][CH3:23])=[O:19])=[C:17]3[C:5]([CH:4]=[CH:3][CH:2]=[CH:1]3)=[N:6][C:7]=2[C:8]2[C:28]1=[CH:12][CH:11]=[CH:10][CH:9]=2

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 14797Potassium HydroxideHCID 178524012HCID 178524012, compound

Product 1

HCID 14366447HCID 14366447, compoundYield 39.3%

Procedure

A mixture of quindoline-11-carboxylic acid (2.6 g, 10 mmol) from Example 1, DMF (25 mL), KOH (2.24 g, 40 mmol), BaO (6.27 g, 40 mmol) and methyl iodide (9.7 mL, 130 mmol) was stirred at room temperature for 48 hours, then partitioned between benzene (60 mL) and water (100 mL). The benzene layer was washed with water (2×60 mL), dried and concentrated. The residue was recrystallized from hexane to afford 1.14 g (39.3%) of the title compound as light yellow crystals, mp 127° C.; 1H NMR (CDCl3) δ 8.49 (d, J=8.0, 1H), 8.31 (d, J=8.0, 1H), 7.95 (d, J=8.4, 1H), 7.68-7.55 (m, 3H), 7.42 (d, J=8.0, 1H), 7.37 (t, J=7.2, 1H), 4.14 (s, 3H), 3.79 (s, 3H); 13C NMR (CDCl3) δ 167.98, 146.93, 145.64, 143.25, 130.27, 129.66, 126.52, 123.55, 122.92, 122.02, 121.28, 120.42, 115.77, 108.70, 52.71, 30.75; MS (EI, M/z) 290.1 (M+)

Workup

  1. custompartitioned between benzene (60 mL) and water (100 mL)
  2. washThe benzene layer was washed with water (2×60 mL)
  3. customdried
  4. concentrationconcentrated
  5. customThe residue was recrystallized from hexane

Sources & evidence

ORD record
ord-a8d9de4b4fa54499ad221d1b2bf75ce1
Source dataset
uspto-grants-1999_07
Patent number
US05925647

Reaction notes

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