Formaldehyde → HCID 178503658, compound

HRID 543688Notes

Reaction equation

HRID 543688 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[C:7]([CH3:12])[CH:8]=[CH:9][CH:10]=2)[N:5]=[CH:4][CH:3]=1.[CH3:13][SH:14].[CH2:15]=O>C(N(CC)CC)C.C(O)C>[OH:1][C:2]1[C:11]2[C:6](=[C:7]([CH3:12])[CH:8]=[CH:9][CH:10]=2)[N:5]=[CH:4][C:3]=1[CH2:13][S:14][CH3:15]

Participants

6

Reactant 3

HCID 712Formaldehyde2×HCID 878Methanethiol2×HCID 178423902HCID 178423902, compound

Product 1

HCID 178503658HCID 178503658, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8471TriethylamineSolvent2×

Procedure

To a stirred suspension of 4-hydroxy-8-methylquinoline (10.0 g.) in triethylamine (8.8 ml.) and industrial methylated spirit (15 ml.) at 0°-5° was added methanethiol (10.4 ml.) followed by aqueous formaldehyde (40%, 14.2 ml.). The mixture was stirred and boiled under reflux for 30 hours. Aqueous formaldehyde (40%, 14.2 ml.) was added dropwise to a stirred solution of triethylamine (8.8 ml.) and methanethiol (10.4 ml.) in ethanol (15 ml.) maintaining the temperature below 10°. The resulting solution was added to the above reaction mixture and the mixture was stirred and boiled under reflux for 20 hours. The mixture was left to cool overnight. The resulting crystalline solid was collected by filtration to give the novel compound 4-hydroxy-8-methyl-3-methylthiomethylquinoline, m.p. 226°-228°.

Workup

  1. temperatureunder reflux for 30 hours
  2. temperaturemaintaining the temperature below 10°
  3. additionThe resulting solution was added to the above reaction mixture
  4. stirringthe mixture was stirred
  5. temperatureunder reflux for 20 hours
  6. waitThe mixture was left
  7. temperatureto cool overnight
  8. filtrationThe resulting crystalline solid was collected by filtration

Sources & evidence

ORD record
ord-571238e02b764ecfbe4b8019da7dd921
Source dataset
uspto-grants-1984_05
Patent number
US04447435

Reaction notes

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