Tetrahydrofuran → HCID 70649684, compound

HRID 869002Notes

Reaction equation

HRID 869002 reaction equation
[CH3:1][C:2]1[N:3]([CH3:15])[C:4]2[C:5]([N:14]=1)=[C:6]1[C:11](=[CH:12][CH:13]=2)[NH:10][CH2:9][CH2:8][CH2:7]1.[OH-:16].[Na+].C(Cl)(=O)O[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.[O:28]1[CH2:32]CC[CH2:29]1>>[CH3:1][C:2]1[N:3]([CH3:15])[C:4]2[C:5]([N:14]=1)=[C:6]1[C:11](=[CH:12][CH:13]=2)[N:10]([C:29]([O:28][CH2:32][C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)=[O:16])[CH2:9][CH2:8][CH2:7]1

Participants

5

Reactant 4

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 15891Phenyl chloroformateHCID 70649687HCID 70649687, compound

Product 1

HCID 70649684HCID 70649684, compound

Conditions

Temperature
0 °C

Procedure

A solution of 2,3-dimethyl-6,7,8,9-tetrahydro-3H-imidazo[4,5-f]quinoline (400 mg, 2 mmol) in tetrahydrofuran (10 mL) was stirred at 0° C. Then NaOH (1 N, 10 mL, 10 mmol) was added to the solution and the mixture was stirred at 0° C. for 10 minutes. Phenyl carbonochloridate (1.02 g, 6 mmol) was then added and the mixture was stirred at 0° C. for 1 hour. The layers were then separated and the water layer was extracted with EtOAc (10 mL×3). The combined organic layers were dried with Na2SO4 and filtered; and the solvent was removed under reduced pressure. The residue was purified with prep-TLC to give the product as a yellow oil (0.53 g). MS (ESI): m/z 336 [M+H]+.

Workup

  1. stirringthe mixture was stirred at 0° C. for 1 hour
  2. customThe layers were then separated
  3. extractionthe water layer was extracted with EtOAc (10 mL×3)
  4. dry with materialThe combined organic layers were dried with Na2SO4
  5. filtrationfiltered
  6. customand the solvent was removed under reduced pressure
  7. customThe residue was purified with prep-TLC

Sources & evidence

ORD record
ord-720f9c628df64a3a85163515e7a2028f
Source dataset
uspto-grants-2015_03
Patent number
US08969349B2

Reaction notes

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