Water → 6-Quinolyl 1-adamantanecarboxylate

HRID 1826872Notes

Reaction equation

HRID 1826872 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-d66b59aea9874beaa366c564a419d9f9
Source dataset
uspto-grants-2006_05
Patent number
US07053104B2

Reaction notes

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