Dimethylamine → 5-Dimethylaminomethyl-8-hydroxy-7-propylquinoline

HRID 34451Notes

Reaction equation

HRID 34451 reaction equation
[OH:1][C:2]1[C:3]([CH2:12][CH2:13][CH3:14])=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][CH:8]=[CH:7]2.[CH3:15][NH:16][CH3:17].[CH2:18]=O>C(O)C>[CH3:15][N:16]([CH2:18][C:5]1[CH:4]=[C:3]([CH2:12][CH2:13][CH3:14])[C:2]([OH:1])=[C:11]2[C:6]=1[CH:7]=[CH:8][CH:9]=[N:10]2)[CH3:17]

Participants

5

Reactant 3

HCID 674DimethylamineHCID 712FormaldehydeHCID 116045138-Hydroxy-7-propylquinoline

Product 1

HCID 201297665-Dimethylaminomethyl-8-hydroxy-7-propylquinolineYield 94.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a cold (0°) solution of 8-hydroxy-7-propylquinoline (5.7 g, 30.4 mmol) and 26% aqueous dimethylamine (15 g, 83 mmol) in 30 mL of ethanol was added dropwise 37% aqueous formaldehyde (4.5 g, 55.4 mmol). After stirring at room temperature for 1 hr, the mixture was refluxed for 2 hr, cooled and evaporated to dryness. The residue was diluted with water, extracted twice with ether and the extracts combined and dried (MgSO4). Evaporation gave 5-dimethylaminomethyl-8-hydroxy-7-propylquinoline as a syrup (7.00 g, 94%), structure confirmed by NMR. A portion of this syrup (2.44 g, 10 mmol) was heated under nitrogen with 2,4-diamino-6-methylthiopyrimidine (1.56 g, 10 mmol) in ethylene glycol (20 mL) at 120°-160° for 1 hr, then cooled. The solid that separated was collected, and washed with ether and hexanes to give the title compound (3.20 g, 90%). An analytical sample was obtained by recrystallization from 95% ethanol, mp. 204°-206° dec. Anal. Calcd for C18H21N5SO: C, 60.82; H, 5.95; N, 19.70; S, 9.02. Found: C, 60.81; H, 5.98; N, 19.67; S, 9.02.

Workup

  1. temperaturethe mixture was refluxed for 2 hr
  2. temperaturecooled
  3. customevaporated to dryness
  4. additionThe residue was diluted with water
  5. extractionextracted twice with ether
  6. dry with materialdried (MgSO4)
  7. customEvaporation

Sources & evidence

ORD record
ord-6ec9cde8de9f48aa9cae768ca420ac26
Source dataset
uspto-grants-1988_08
Patent number
US04761475

Reaction notes

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