3-Chloro-1-butene → HCID 10036173, compound

HRID 1611702Notes

Reaction equation

HRID 1611702 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[C:5]([OH:12])[CH:6]=[CH:7][CH:8]=2)[N:3]=1.C([O-])([O-])=O.[K+].[K+].Cl[CH:20]([CH3:23])[CH:21]=[CH2:22]>C(O)C>[CH2:23]([O:12][C:5]1[CH:6]=[CH:7][CH:8]=[C:9]2[C:4]=1[N:3]=[C:2]([NH2:1])[CH:11]=[CH:10]2)/[CH:20]=[CH:21]/[CH3:22]

Participants

5

Reactant 3

HCID 112423-Chloro-1-buteneHCID 11430Potassium CarbonateHCID 46537882-Amino-8-quinolinol2×

Product 1

HCID 10036173HCID 10036173, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
65 °C

Procedure

A 250 mL round bottom flask was charged with 2.00 g (12.5 mmol) of 2-amino-8-hydroxyquinoline, 3.46 g (25.0 mmol), of K2CO3 and 63 mL of anhydr ethanol. Following the dissolution of 2-amino-8-hydroxyquinoline, 1.51 mL of 3-chloro-1-butene (15.0 mmol) was added in one portion, and the mixture was heated to 65° C. in an oil bath. After 48 h, the solvent was evaporated and the residue dissolved in EtOAc and washed with H2O. The combined aqueous layers were back-extracted with EtOAc. The organic layers were then pooled, dried, and filtered. The residue was then purified by column chromatography (SiO2; EtOAc/hexanes with 0.1% Et3N). The resultant material was then re-crystallized from Et2O to afford the title compound. 1H NMR (300 MHz, DMSO-d6) δ ppm 7.82 (m, 1H), 7.16 (m, 1H), 7.00 (m, 2H), 6.73 (m, 1H), 6.39 (m, 2H), 5.67–5.98 (m, 2H), 4.44–4.67 (m, 2H), 1.74 (m, 3H); MS (DCI/NH3) m/z 215 [M+H]+.

Workup

  1. additionwas added in one portion
  2. customthe solvent was evaporated
  3. dissolutionthe residue dissolved in EtOAc
  4. washwashed with H2O
  5. extractionThe combined aqueous layers were back-extracted with EtOAc
  6. customdried
  7. filtrationfiltered
  8. customThe residue was then purified by column chromatography (SiO2; EtOAc/hexanes with 0.1% Et3N)
  9. customThe resultant material was then re-crystallized from Et2O

Sources & evidence

ORD record
ord-c74b1390ab32473383c417a511dd2ad0
Source dataset
uspto-grants-2006_01
Patent number
US06989392B2

Reaction notes

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