3-Amino-1-propanol → HCID 18403990, compound

HRID 1017625Notes

Reaction equation

HRID 1017625 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[C:4]([C:12]2[CH:21]=[CH:20][C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH:13]=2)[CH:3]=1.[NH2:22][CH2:23][CH2:24][CH2:25][OH:26]>>[OH:26][CH2:25][CH2:24][CH2:23][NH:22][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[C:4]([C:12]2[CH:21]=[CH:20][C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH:13]=2)[CH:3]=1

Participants

3

Reactant 2

HCID 90863-Amino-1-propanolHCID 12116223QUINOLINE, 4-CHLORO-2-(2-NAPHTHALENYL)-

Product 1

HCID 18403990HCID 18403990, compound

Procedure

A solution of 4-chloro-(2-napthyl) quinoline (420 mg, 1.4 mmol) in 3-aminopropanol (1.0 mL) was heated to 130° C. for 1.5 h under a nitrogen atmosphere. Treatment with water (2 mL) was followed by extraction of the mixture with AcOEt, drying of the extract with MgSO4, and concentration to give a residue of crude N-(3-hydroxypropyl)-2-(2-naphthyl)quinolin-4-amine. This compound was purified by silica gel chromatography eluting with CH2Cl2/MeOH (5:1) followed by crystallization of its hydrobromide salt; yield 82% of C22H20N2O.HBr.H2O; mp 230-235° C. Anal. Calcd for C22H20N2O.HBr.H2O: C, 61.82: H, 5.43; N, 6.55. Found: C, 61.98; H, 5.28; N, 6.49.

Workup

  1. extractionTreatment with water (2 mL) was followed by extraction of the mixture with AcOEt
  2. customdrying of the
  3. extractionextract with MgSO4, and concentration

Sources & evidence

ORD record
ord-8b6ae0d8efd2438ca34a00be197ba2bb
Source dataset
uspto-grants-2002_11
Patent number
US06479504B1

Reaction notes

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