Acetic Anhydride → HCID 86612247, compound

HRID 1623113Notes

Reaction equation

HRID 1623113 reaction equation
C(N(CC)CC)C.[CH3:8][O:9][NH:10][CH2:11][CH2:12][CH2:13][CH2:14][N:15]1[C:27]2[C:26]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[N:20]=[CH:19][C:18]=2[N:17]=[C:16]1[CH2:28][CH2:29][CH3:30].[C:31](OC(=O)C)(=[O:33])[CH3:32]>ClCCl.C(=O)(O)[O-].[Na+]>[CH3:8][O:9][N:10]([CH2:11][CH2:12][CH2:13][CH2:14][N:15]1[C:27]2[C:26]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[N:20]=[CH:19][C:18]=2[N:17]=[C:16]1[CH2:28][CH2:29][CH3:30])[C:31](=[O:33])[CH3:32]

Participants

6

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 86052872HCID 86052872, compound

Product 1

HCID 86612247HCID 86612247, compoundYield 98.7%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
0 °C

Procedure

Triethylamine (0.167 mL, 1.2 mmol) was added to O-methyl-N-[4-(2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)butyl]hydroxylamine (0.32 g, 1.0 mmol) in dichloromethane (10 mL) and cooled to 0° C. Acetic anhydride (0.103 mL, 1.1 mmol) was added dropwise and the reaction mixture was stirred for 6 hours. The reaction was then diluted with dichloromethane (40 mL) and saturated aqueous sodium bicarbonate (10 mL) and stirred overnight. The phases were separated and the aqueous phase was extracted with dichloromethane (50 mL). The combined organics were dried over potassium carbonate, filtered, and concentrated to afford 0.35 g of N-methoxy-N-[4-(2-propy-1H-imidazo[4,5-c]quinolin-1-yl)butyl]acetamide.

Workup

  1. stirringstirred overnight
  2. customThe phases were separated
  3. extractionthe aqueous phase was extracted with dichloromethane (50 mL)
  4. dry with materialThe combined organics were dried over potassium carbonate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-352ebffadd0b4fa9a37a045da1fecd8d
Source dataset
uspto-grants-2014_07
Patent number
US08778963B2

Reaction notes

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