N,N-Diethylaniline → HCID 11369604, compound

HRID 2244576Notes

Reaction equation

HRID 2244576 reaction equation
[CH3:1][N:2]([CH3:20])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:10]=[C:11](O)[C:12]3[CH:13]=[CH:14][CH:15]=[N:16][C:17]=3[CH:18]=2)=[CH:5][CH:4]=1.C(N(CC)C1C=CC=CC=1)C.O=P(Cl)(Cl)[Cl:34]>>[Cl:34][C:11]1[N:10]=[C:9]([C:6]2[CH:7]=[CH:8][C:3]([N:2]([CH3:20])[CH3:1])=[CH:4][CH:5]=2)[CH:18]=[C:17]2[C:12]=1[CH:13]=[CH:14][CH:15]=[N:16]2

Participants

4

Reactant 3

HCID 7061N,N-DiethylanilineHCID 24813Phosphorus oxychlorideHCID 178482629HCID 178482629, compound

Product 1

HCID 11369604HCID 11369604, compound

Conditions

Temperature
110 °C

Procedure

A mixture of 7-(4-dimethylaminophenyl)-[1,6]naphthyridin-5-ol (Example 1) (1.2 g, 5 mmol), POCl3 (10 mL) and N,N-diethylaniline (0.15 g, 1.0 mmol) were stirred at 110° C. for 16 hours. The contents were cooled to room temperature and excess POCl3 was removed in vacuo. The residue was quenched with water and neutralized with aqueous sodium carbonate. The aqueous solution was then extracted with dichloromethane (2×30 mL). The combined organic extracts were dried over anhydrous magnesium sulfate and concentrated in vacuo to give a tan oil. Purification by flash chromatography eluting with hexanes/EtOAc (1:1) afforded the title compound as a yellowish solid (1.1 g). 1H NMR (CDCl3, 400 MHz) δ 9.03 (dd, 1H), 8.54 (d, 1H), 8.13 (s, 1H), 8.08 (d, 2H), 7.46 (dd, 1H), 6.81 (d, 2H), 3.05 (s, 6H).

Workup

  1. temperatureThe contents were cooled to room temperature
  2. customexcess POCl3 was removed in vacuo
  3. customThe residue was quenched with water and neutralized with aqueous sodium carbonate
  4. extractionThe aqueous solution was then extracted with dichloromethane (2×30 mL)
  5. dry with materialThe combined organic extracts were dried over anhydrous magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. customto give a tan oil
  8. customPurification by flash chromatography
  9. washeluting with hexanes/EtOAc (1:1)

Sources & evidence

ORD record
ord-e4853ef527b344c5a1011e5014a2fc69
Source dataset
uspto-grants-2010_03
Patent number
US07678911B2

Reaction notes

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