Acetic Acid → HCID 86052872, compound

HRID 1623112Notes

Reaction equation

HRID 1623112 reaction equation
C([BH3-])#N.[Na+].C(O)(=O)C.[CH3:9][O:10][N:11]=[CH:12][CH2:13][CH2:14][CH2:15][N:16]1[C:28]2[C:27]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[N:21]=[CH:20][C:19]=2[N:18]=[C:17]1[CH2:29][CH2:30][CH3:31].C(=O)([O-])[O-].[K+].[K+]>C(O)C.O.ClCCl>[CH3:9][O:10][NH:11][CH2:12][CH2:13][CH2:14][CH2:15][N:16]1[C:28]2[C:27]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[N:21]=[CH:20][C:19]=2[N:18]=[C:17]1[CH2:29][CH2:30][CH3:31]

Participants

8

Reactant 4

HCID 176Acetic AcidHCID 11430Potassium CarbonateHCID 5003444Sodium cyanoborohydrideHCID 86052868HCID 86052868, compound

Product 1

HCID 86052872HCID 86052872, compound

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
100 °C

Procedure

Sodium cyanoborohydride (0.22 g, 3.5 mmol) and acetic acid (2 mL) were added to 4-(2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)butyraldehyde O-methyloxime in ethanol (6 mL) and stirred for 2 hours. The pH of the reaction mixture was made basic with potassium carbonate and the reaction mixture was diluted with water (5 mL) and dichloromethane (50 mL). The layers were separated, and the organic layer was dried over potassium carbonate, filtered, and concentrated under reduced pressure to afford 0.62 g of crude material with a small amount of ethanol present. Silica gel (1 g) was added to the crude material and the mixture was heated for 2.5 hours at 100° C. The mixture was cooled and the material was filtered with a 1:1 mixture of dichloromethane and methanol. The filtrate was concentrated under reduced pressure to afford 0.35 g of O-methyl-N-[4-(2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)butyl]hydroxylamine as an oil.

Workup

  1. customThe layers were separated
  2. dry with materialthe organic layer was dried over potassium carbonate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customto afford 0.62 g of crude material with a small amount of ethanol present
  6. temperatureThe mixture was cooled
  7. filtrationthe material was filtered with a 1:1 mixture of dichloromethane and methanol
  8. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-85b5ffadfb02400baad283aa8fe7a70e
Source dataset
uspto-grants-2014_07
Patent number
US08778963B2

Reaction notes

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