HCID 67776917, compound → HCID 67774118, compound

HRID 511647Notes

Reaction equation

HRID 511647 reaction equation
[CH3:1][C:2]1([C:6]2[CH:12]=[CH:11][C:9]([NH2:10])=[C:8]([N+:13]([O-])=O)[CH:7]=2)[CH2:5][CH2:4][CH2:3]1>[Pd].C(O)C>[CH3:1][C:2]1([C:6]2[CH:7]=[C:8]([NH2:13])[C:9]([NH2:10])=[CH:11][CH:12]=2)[CH2:3][CH2:4][CH2:5]1

Participants

4

Reactant 1

HCID 67776917HCID 67776917, compound

Product 1

HCID 67774118HCID 67774118, compoundYield 101.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent2×

Procedure

A solution of 4-(1-methylcyclobutyl)-2-nitroaniline (138 mg. 0.668 mmol) in ethanol (8.5 mL, 140 mmol) was carefully treated with 10% Palladium on Carbon (14.2 mg, 0.0134 mmol) as a slurry in ethanol. The reaction flask was evacuated and filled with hydrogen gas three times and the reaction mixture was stirred under an atmosphere of Hydrogen for 4 h. The reaction mixture was filtered through a pad of solka Floc® and the pad was washed with 20 ml MeOH. The filtrate was concentrated to yield an oil which was placed under high vacuum yielding the desired compound as a solid (119 mg) which was used directly in the next step. 1H NMR (400 MHZ. CDCl3) δH ppm 6.66 (m, 1H), 6.53 (m, 2H), 3.34 (br. s., 4H), 2.33 (m, 2H), 2.08 (m, 1H), 1.99 (m. 2H). 1.80 (m, 1H), 1.42 (s, 3H).

Workup

  1. customThe reaction flask was evacuated
  2. additionfilled with hydrogen gas three times
  3. filtrationThe reaction mixture was filtered through a pad of solka Floc®
  4. washthe pad was washed with 20 ml MeOH
  5. concentrationThe filtrate was concentrated
  6. customto yield an oil which

Sources & evidence

ORD record
ord-c07d08742a3045d7a73ad9b90b7ba0f1
Source dataset
uspto-grants-2015_08
Patent number
US09096634B2

Reaction notes

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