Potassium Hydroxide → HCID 57031936, compound

HRID 1968534Notes

Reaction equation

HRID 1968534 reaction equation
[OH:1][C:2]1([C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=2[NH:12]C=O)[CH2:5][CH2:4][CH2:3]1.[OH-].[K+]>CO.O>[NH2:12][C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=1[C:2]1([OH:1])[CH2:5][CH2:4][CH2:3]1

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 59620275N-[2-(1-Hydroxycyclobutyl)phenyl]formamide

Product 1

HCID 57031936HCID 57031936, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

N-(2-(1-hydroxycyclobutyl)phenyl)formamide (103 mg, 0.539 mmol) and potassium hydroxide (0.015 mL, 0.539 mmol) were combined in methanol (3 mL) and the mixture was heated to reflux for 3 hours. The reaction mixture was diluted with H2O (25 mL) and extracted with ethyl acetate (3×25 mL). The combined organic layers were dried (Na2SO4), filtered and concentrated. The product was purified by flash chromatography (Analogix, 0 to 40% ethyl acetate in hexanes over 25 minutes, 4 g silica, 18 mL/minutes) to give 1-(2-aminophenyl)cyclobutanol.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 3 hours
  3. extractionextracted with ethyl acetate (3×25 mL)
  4. dry with materialThe combined organic layers were dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe product was purified by flash chromatography (Analogix, 0 to 40% ethyl acetate in hexanes over 25 minutes, 4 g silica, 18 mL/minutes)

Sources & evidence

ORD record
ord-fcdaafbb678c48e782e6156e9913ac97
Source dataset
uspto-grants-2013_04
Patent number
US08426408B2

Reaction notes

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