3-Amino-1-propanol → HCID 19369772, compound

HRID 849204Notes

Reaction equation

HRID 849204 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:20]2[C:19]3[CH:18]=[CH:17][CH:16]=[C:15]([O:21][CH2:22][C:23]([F:26])([F:25])[F:24])[C:14]=3[N:13]=[C:12](Cl)[C:11]=2[CH:10]=[CH:9]1.[NH2:28][CH2:29][CH2:30][CH2:31][OH:32]>>[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:20]2[C:19]3[CH:18]=[CH:17][CH:16]=[C:15]([O:21][CH2:22][C:23]([F:26])([F:25])[F:24])[C:14]=3[N:13]=[C:12]([NH:28][CH2:29][CH2:30][CH2:31][OH:32])[C:11]=2[CH:10]=[CH:9]1

Participants

3

Reactant 2

HCID 90863-Amino-1-propanolHCID 19369813HCID 19369813, compound

Product 1

HCID 19369772HCID 19369772, compound

Conditions

Temperature
180 °C

Procedure

1-(2-Methylphenyl)-4-chloro-6-β,β,β-trifluoroethoxypyrrolo[3,2-c]quinoline(600 mg, 1.5 mmol), prepared by the procedures of Step 1 and Step 2 in the Example 34, was dissolved in 3-amino-1-propanol(10 ml) in the pressure tube, and the resultant was refluxed at 180° C. for 3 hours. After removing the excess 3-amino-1-propanol by distillation under reduced pressure, the residue was diluted in dichloromethane(20 ml), and washed with water(15 ml) for 3 times. The organic layer was dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by silica gel chromatography to obtain 522 mg of desired compound as solid in 81% of yield.

Workup

  1. customAfter removing the excess 3-amino-1-propanol
  2. distillationby distillation under reduced pressure
  3. additionthe residue was diluted in dichloromethane(20 ml)
  4. washwashed with water(15 ml) for 3 times
  5. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-b8146a79c14c4c6da72e0adb16749501
Source dataset
uspto-grants-2000_01
Patent number
US06011044

Reaction notes

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