Water → HCID 66688776, compound

HRID 337101Notes

Reaction equation

HRID 337101 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1([C:13]#[N:14])[CH2:12][CH2:11][CH2:10]1.S(=O)(=O)(O)[OH:16].O>C(O)(=O)C>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1([C:13]([NH2:14])=[O:16])[CH2:12][CH2:11][CH2:10]1

Participants

5

Reactant 3

HCID 962WaterHCID 1118Sulfuric AcidHCID 389971951-(2-Methoxyphenyl)cyclobutane-1-carbonitrile

Product 1

HCID 66688776HCID 66688776, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
60 °C

Procedure

To 1-(2-methoxyphenyl)cyclobutanecarbonitrile (4.29 g) was added sulfuric acid (20 mL, 95-98%)/water (20 mL) and the reaction warmed to 60° C. After 1 h the solution was warmed to 80° C. and heating was continued for 3 h. The reaction was cooled to room temperature and stirred for 16 h. Heating was resumed and after 1 h acetic acid (10 mL) was added. The temperature was increased to 90° C. and heating was continued for 1.75 h. The reaction was cooled to room temperature and then poured onto ˜300 ml of ice and extracted with ethyl acetate. The organic layer was dried (Na2SO4) and the solvent removed in vacuo to afford the subtitle product (4.19 g).

Workup

  1. temperatureAfter 1 h the solution was warmed to 80° C.
  2. temperatureheating
  3. temperatureThe reaction was cooled to room temperature
  4. temperatureHeating
  5. waitwas resumed and after 1 h
  6. temperatureThe temperature was increased to 90° C.
  7. temperatureheating
  8. waitwas continued for 1.75 h
  9. temperatureThe reaction was cooled to room temperature
  10. extractionextracted with ethyl acetate
  11. dry with materialThe organic layer was dried (Na2SO4)
  12. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-b72c737c480d483a97749d4040d804f7
Source dataset
uspto-grants-2014_11
Patent number
US08889692B2

Reaction notes

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