Trimethyl orthovalerate → HCID 22254509, compound

HRID 1839124Notes

Reaction equation

HRID 1839124 reaction equation
[O:1]([CH2:8][CH2:9][NH:10][C:11]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[N:14]=[CH:13][C:12]=1[NH2:21])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CO[C:24](OC)(OC)[CH2:25][CH2:26][CH2:27][CH3:28]>>[CH2:25]([C:24]1[N:10]([CH2:9][CH2:8][O:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[C:11]2[C:20]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[N:14]=[CH:13][C:12]=2[N:21]=1)[CH2:26][CH2:27][CH3:28]

Participants

3

Reactant 2

HCID 83755Trimethyl orthovalerateHCID 12114241HCID 12114241, compound

Product 1

HCID 22254509HCID 22254509, compoundYield 96.5%

Procedure

N4-(2-Phenoxyethyl)quinoline-3,4-diamine (2.0 g, 7.2 mmol), xylenes (150 ml), and trimethylorthovalerate (2.5 ml, 14.3 mmol) were combined under an atmosphere of nitrogen and heated at reflux temperature for 4 days. The external heat was increased and approximately 35 ml of xylenes was removed by distillation. The reaction was slowly cooled to room temperature and a precipitate formed. The solid was recovered by vacuum filtration to yield 2.4 g of 2-butyl-1-(2-phenoxyethyl)-1H-imidazo[4,5-c]quinoline as a light tan crystalline solid.

Workup

  1. temperatureheated
  2. temperatureat reflux temperature for 4 days
  3. temperatureThe external heat
  4. temperaturewas increased
  5. customapproximately 35 ml of xylenes was removed by distillation
  6. customa precipitate formed
  7. filtrationThe solid was recovered by vacuum filtration

Sources & evidence

ORD record
ord-1b7e6b3b17f147b7b158f4b3fbd937ec
Source dataset
uspto-grants-2004_01
Patent number
US06677348B2

Reaction notes

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