5,6,7,8-Tetrahydro-1-naphthol → 5,6,7,8-Tetrahydro-1-naphthyl-nicotinate

HRID 2413859Notes

Reaction equation

HRID 2413859 reaction equation
[C:1]1([OH:11])[C:10]2[CH2:9][CH2:8][CH2:7][CH2:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.Cl.[C:13](Cl)(=[O:20])[C:14]1[CH:19]=[CH:18][CH:17]=[N:16][CH:15]=1>N1C=CC=CC=1>[C:1]1([O:11][C:13](=[O:20])[C:14]2[CH:19]=[CH:18][CH:17]=[N:16][CH:15]=2)[C:10]2[CH2:9][CH2:8][CH2:7][CH2:6][C:5]=2[CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 682585,6,7,8-Tetrahydro-1-naphtholHCID 884383-Pyridinecarbonyl chloride, hydrochloride (1:1)

Product 1

HCID 129401155,6,7,8-Tetrahydro-1-naphthyl-nicotinate

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
30 °C

Procedure

7 g (47 mmol) of 5,6,7,8-tetrahydro-1-naphthol and 9 g (50 mmol) of nicotinic acid chloride hydrochloride was mixed with 130 ml of dry pyridine and stirred for 24 hours at 30° C. After cooling precipitated pyridine hydrochloride was sucked off, and the filtrate mixed with 300 ml of water. The precipitated raw product was washed with two 200 ml portions of water and recrystallized from methanol.

Workup

  1. temperatureAfter cooling
  2. customprecipitated pyridine hydrochloride
  3. additionthe filtrate mixed with 300 ml of water
  4. customThe precipitated raw product
  5. washwas washed with two 200 ml portions of water
  6. customrecrystallized from methanol

Sources & evidence

ORD record
ord-cc52475dff5041d59bcf1b714c83f048
Source dataset
uspto-grants-1988_01
Patent number
USRE032581

Reaction notes

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