Water → 6-Quinolyl 1-adamantanecarboxylate

HRID 2302029Notes

Reaction equation

HRID 2302029 reaction equation
[C:1]12([C:11](Cl)=[O:12])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.[OH:14][C:15]1[CH:16]=[C:17]2[C:22](=[CH:23][CH:24]=1)[N:21]=[CH:20][CH:19]=[CH:18]2.O>N1C=CC=CC=1>[C:1]12([C:11]([O:14][C:15]3[CH:16]=[C:17]4[C:22](=[CH:23][CH:24]=3)[N:21]=[CH:20][CH:19]=[CH:18]4)=[O:12])[CH2:8][CH:7]3[CH2:6][CH:5]([CH2:4][CH:3]([CH2:9]3)[CH2:2]1)[CH2:10]2

Participants

5

Reactant 3

HCID 962WaterHCID 113746-HydroxyquinolineHCID 989151-Adamantanecarbonyl chloride

Product 1

HCID 120427526-Quinolyl 1-adamantanecarboxylate

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Procedure

1-Adamantanecarbonyl chloride (1.37 g, 6.90 mmol) in pyridine (5 mL) was added to a solution of 6-hydroxyquinoline (1.00 g, 6.89 mmol) in pyridine (15 mL). The reaction was stirred for 16 h. To the stirring reaction mixture was added water (200 mL) which caused the product to precipitate. This precipitate was filtered, washed with water (3×50 mL), and dried under high vacuum. This provided 1.56 g (73.7%) of (41) as a light-brown powder:

Workup

  1. customTo the stirring reaction mixture
  2. customto precipitate
  3. filtrationThis precipitate was filtered
  4. washwashed with water (3×50 mL)
  5. customdried under high vacuum

Sources & evidence

ORD record
ord-0d39146b5fda42fa81d44bdf3758a7ff
Source dataset
uspto-grants-2002_08
Patent number
US06429207B1

Reaction notes

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