HCID 67776917, compound → HCID 67774118, compound

HRID 2040688Notes

Reaction equation

HRID 2040688 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, 1 H), 6.53 (m, 2 H), 3.34 (br. s., 4 H), 2.33 (m, 2 H), 2.08 (m, 1 H), 1.99 (m. 2 H). 1.80 (m, 1H), 1.42 (s, 3 H).

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-c4ec741c854e4a58a34fd019c79543a0
Source dataset
uspto-grants-2013_11
Patent number
US08580762B2

Reaction notes

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