Pyridinium chloride → HCID 70087059, compound

HRID 1456032Notes

Reaction equation

HRID 1456032 reaction equation
[CH2:1]([N:3]1[C:7]2=[N:8][C:9]3[C:14]([C:15]([NH:16][CH2:17][C:18]4[CH:23]=[CH:22][CH:21]=[C:20]([O:24]C)[CH:19]=4)=[C:6]2[CH:5]=[N:4]1)=[CH:13][CH:12]=[CH:11][CH:10]=3)[CH3:2].Cl.N1C=CC=CC=1>[OH-].[Na+]>[CH2:1]([N:3]1[C:7]2=[N:8][C:9]3[C:14]([C:15]([NH:16][CH2:17][C:18]4[CH:23]=[CH:22][CH:21]=[C:20]([OH:24])[CH:19]=4)=[C:6]2[CH:5]=[N:4]1)=[CH:13][CH:12]=[CH:11][CH:10]=3)[CH3:2]

Participants

4

Reactant 2

HCID 10176127Pyridinium chlorideHCID 19592237HCID 19592237, compound

Product 1

HCID 70087059HCID 70087059, compound

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Conditions

Temperature
200 °C

Procedure

A mixture of 1-ethyl-N-(3-methoxyphenylmethyl)-1H-pyrazolo[3,4-b]quinolin-4-amine (3.8 g, 0.0114 mol) and pyridine hydrochloride (10 g) was heated at about 200° C. for 3 hours. The reaction mixture was cooled and then 10% NaOH (70 mL) was added. The mixture was washed with ether (2×30 mL) and then the aqueous layer was acidified with acetic acid to a pH of about 5. The solid which formed was collected by filtration and dried in vacuo to afford 2.5-3 g of 1-ethyl-N-(3-hydroxyphenylmethyl)-1H-pyrazolo[3,4-b]quinolin-4-amine, as an off-white solid, m.p. 273°-275° C.

Workup

  1. temperatureThe reaction mixture was cooled
  2. washThe mixture was washed with ether (2×30 mL)
  3. customThe solid which formed
  4. filtrationwas collected by filtration
  5. customdried in vacuo

Sources & evidence

ORD record
ord-b711a92a05674693b0598842f35d19c2
Source dataset
uspto-grants-1998_12
Patent number
US05843956

Reaction notes

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