HCID 178526652, compound → HCID 178507665, compound

HRID 1370106Notes

Reaction equation

HRID 1370106 reaction equation
[OH:1][C@H:2]1[CH2:7][CH2:6][C@H:5]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([C:15]([F:18])([F:17])[F:16])=[CH:11][C:10]=2[N+:19]([O-])=O)[CH2:4][CH2:3]1>[Pd].CO.O1CCOCC1>[NH2:19][C:10]1[CH:11]=[C:12]([C:15]([F:16])([F:17])[F:18])[CH:13]=[CH:14][C:9]=1[NH:8][C@H:5]1[CH2:6][CH2:7][C@H:2]([OH:1])[CH2:3][CH2:4]1

Participants

5

Reactant 1

HCID 178526652HCID 178526652, compound

Product 1

HCID 178507665HCID 178507665, compoundYield 97.1%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

A mixture of 4-(trans-4-hydroxycyclohexylamino)-3-nitrobenzotrifluoride (4.0 g) and 10% palladium on activated carbon (400 mg) in a mixture of methanol (20 mL) and dioxane(20 mL) was stirred under hydrogen atmosphere (3 atm) at ambient temperature for 4 hours. The reaction mixture was filtered through a celite pad, and the filtrate was concentrated in vacuo. The residue was subjected to a silica gel column chromatography eluting with a mixture of chloroform and methanol (20:1). The obtained substance was triturated with petroleum ether to give 3-amino-4-(trans-4-hydroxycyclohexylamino)benzotrifluoride (3.5 g) as a pale orange solid.

Workup

  1. filtrationThe reaction mixture was filtered through a celite pad
  2. concentrationthe filtrate was concentrated in vacuo
  3. washeluting with a mixture of chloroform and methanol (20:1)
  4. customThe obtained substance was triturated with petroleum ether

Sources & evidence

ORD record
ord-66c3eb82e2b449eca19504b0ede5eac6
Source dataset
uspto-grants-2003_06
Patent number
US06582351B1

Reaction notes

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