Formaldehyde → HCID 71295622, compound

HRID 1774671Notes

Reaction equation

HRID 1774671 reaction equation
[Si:1]([O:8][C:9]1[CH:18]=[C:17]2[C:12]([CH2:13][CH2:14][C:15](=[O:19])[NH:16]2)=[CH:11][CH:10]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[CH2:20]=[O:21].C(N(CC)CC)C.O>CN(C=O)C>[Si:1]([O:8][C:9]1[CH:18]=[C:17]2[C:12]([CH2:13][CH2:14][C:15](=[O:19])[N:16]2[CH2:20][OH:21])=[CH:11][CH:10]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 962WaterHCID 8471TriethylamineHCID 71295385HCID 71295385, compound

Product 1

HCID 71295622HCID 71295622, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

7-(tert-Butyl-dimethylsilanyloxy)-3,4-dihydro-1H-quinolin-2-one (830 mg) was suspended in DMF (13 ml), formaldehyde (4.3 ml) and triethylamine (0.083 ml) were added, and the mixture was stirred at 80° C. overnight. After cooling to room temperature, water was added, and the mixture was extracted with ethyl acetate, dried over sodium sulfate, and purified by moderate-pressure silica gel column chromatography (hexane:ethyl acetate=2:1) to give the title compound (36 mg) as white crystals.

Workup

  1. temperatureAfter cooling to room temperature
  2. extractionthe mixture was extracted with ethyl acetate
  3. dry with materialdried over sodium sulfate
  4. custompurified by moderate-pressure silica gel column chromatography (hexane:ethyl acetate=2:1)

Sources & evidence

ORD record
ord-afec9ab94ef842abb2f4d6f60bab1acb
Source dataset
uspto-grants-2016_02
Patent number
US09260420B2

Reaction notes

Loading…