Water → HCID 22136372, compound

HRID 1826874Notes

Reaction equation

HRID 1826874 reaction equation
Cl.[N:2]1[C:11]2[C:6](=[CH:7][C:8]([C:12](Cl)=[O:13])=[CH:9][CH:10]=2)[CH:5]=[CH:4][CH:3]=1.[C:15]12([OH:25])[CH2:24][CH:19]3[CH2:20][CH:21]([CH2:23][CH:17]([CH2:18]3)[CH2:16]1)[CH2:22]2.O>N1C=CC=CC=1>[N:2]1[C:11]2[C:6](=[CH:7][C:8]([C:12]([O:25][C:15]34[CH2:22][CH:21]5[CH2:20][CH:19]([CH2:18][CH:17]([CH2:23]5)[CH2:16]3)[CH2:24]4)=[O:13])=[CH:9][CH:10]=2)[CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 641521-AdamantanolHCID 22136358Quinoline-6-carbonyl chloride--hydrogen chloride (1/1)

Product 1

HCID 22136372HCID 22136372, compoundYield 31.5%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Conditions

Temperature
70 °C

Procedure

6-Quinolinecarbonyl chloride hydrochloride (0.76 g, 3.3 mmol) in pyridine (2 mL) was added to a solution of 1-adamantanol (0.60 g, 3.9 mmol) in pyridine (8 mL). The reaction was stirred at 70° C. for 16 h. To the stirring reaction mixture was added water (100 mL) which caused the product to precipitate. This precipitate was filtered and then washed with water (3×25 mL). The filter cake was dissolved in ethanol (20 mL) and water was then added to the cloud point (16 mL). The crystallizing solution was allowed to stand for 15 h. Filtering and drying under high vacuum for 7 h provided 0.32 g (26%) of (61) as light brown needle-like crystals:

Workup

  1. customTo the stirring reaction mixture
  2. customto precipitate
  3. filtrationThis precipitate was filtered
  4. washwashed with water (3×25 mL)
  5. dissolutionThe filter cake was dissolved in ethanol (20 mL)
  6. additionwater was then added to the cloud point (16 mL)
  7. waitto stand for 15 h
  8. filtrationFiltering
  9. customdrying under high vacuum for 7 h

Sources & evidence

ORD record
ord-96bee3001af4484ca83846fc6cd86274
Source dataset
uspto-grants-2006_05
Patent number
US07053104B2

Reaction notes

Loading…