Pyridinium chloride → HCID 136119078, compound

HRID 1597961Notes

Reaction equation

HRID 1597961 reaction equation
Cl.[Cl:2][C:3]1[CH:11]=[C:10]2[C:6]([CH2:7][CH2:8][N:9]2[C:12]2[C:21]3[C:16](=[CH:17][C:18]([O:22]C)=[CH:19][CH:20]=3)[N:15]=[CH:14][N:13]=2)=[CH:5][CH:4]=1.Cl.N1C=CC=CC=1>>[Cl:2][C:3]1[CH:11]=[C:10]2[C:6]([CH2:7][CH2:8][N:9]2[C:12]2[C:21]3[C:16](=[CH:17][C:18]([OH:22])=[CH:19][CH:20]=3)[N:15]=[CH:14][N:13]=2)=[CH:5][CH:4]=1

Participants

3

Reactant 2

HCID 10176127Pyridinium chlorideHCID 18932847HCID 18932847, compound

Product 1

HCID 136119078HCID 136119078, compound

Procedure

4-(6-Chloro-2,3-dihydro-indol-1-yl)-7-methoxy-quinazoline (7.596 g, 24.4 mmol; free-base from Example 64) was added in several portions over 5 minutes to molten pyridine hydrochloride (85 g) at 170° C. The stoppered mixture was heated 75 minutes and then poured into ice/water (~600 mL). The precipitated solid was filtered, dissolved in 10% i-PrOH/CHCl3, and the organic solution was washed with saturated aqueous NaHCO3 and brine, dried over Na2SO4(s), filtered and concentrated in vacuo to afford 3.14 g. of product. (M.P. 270°-280° C. (dec); LC-MS: 298 (MH+); anal. RP18-HPLC RT: 4.00 min.).

Workup

  1. customat 170° C
  2. temperatureThe stoppered mixture was heated 75 minutes
  3. filtrationThe precipitated solid was filtered
  4. dissolutiondissolved in 10% i-PrOH/CHCl3
  5. washthe organic solution was washed with saturated aqueous NaHCO3 and brine
  6. dry with materialdried over Na2SO4(s)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customto afford 3.14 g

Sources & evidence

ORD record
ord-812551f267f14a99afa6e427ec0e4ceb
Source dataset
uspto-grants-1998_04
Patent number
US05736534

Reaction notes

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