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1-(4-(Benzyloxy)-5-methoxy-2-nitrophenyl)-cyclobutanecarbonitrile → 1-(4-Hydroxy-5-methoxy-2-nitrophenyl)cyclobutanecarbonitrile

HRID 925122
Notes
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Reaction equation

HRID 925122 reaction equation
C([O:8][C:9]1[C:14]([O:15][CH3:16])=[CH:13][C:12]([C:17]2([C:21]#[N:22])[CH2:20][CH2:19][CH2:18]2)=[C:11]([N+:23]([O-:25])=[O:24])[CH:10]=1)C1C=CC=CC=1.[H][H]>CCO.[Pd]>[OH:8][C:9]1[C:14]([O:15][CH3:16])=[CH:13][C:12]([C:17]2([C:21]#[N:22])[CH2:18][CH2:19][CH2:20]2)=[C:11]([N+:23]([O-:25])=[O:24])[CH:10]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 1010436161-(4-(Benzyloxy)-5-methoxy-2-nitrophenyl)-cyclobutanecarbonitrileHCID 178418361HCID 178418361, compound

Product 1

HCID 921351291-(4-Hydroxy-5-methoxy-2-nitrophenyl)cyclobutanecarbonitrileYield 99%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

A solution of 1-(4-(benzyloxy)-5-methoxy-2-nitrophenyl)cyclobutanecarbonitrile (2.78 g, 8.22 mmol), from Step 2, in EtOH (30 mL) was treated with 10% Pd/C (0.87 g, 0.822 mmol), fitted with hydrogen filled balloon and heated to 70° C. for 3 hours under hydrogen atmosphere. The catalyst was filtered off and washed with EtOH. Solvent was concentrated to provide 1-(4-(hydroxyl)-5-methoxy-2-nitrophenyl)cyclobutanecarbonitrile (2 g, 99%). MS (ESI) m/z 249 (M+H)+.

Workup

  1. filtrationThe catalyst was filtered off
  2. washwashed with EtOH
  3. concentrationSolvent was concentrated

Sources & evidence

ORD record
ord-33c61dc6ceca4f408ae5c37228645f07
Source dataset
uspto-grants-2016_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09284272B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes