Ethanol → HCID 80457062, compound

HRID 1618928Notes

Reaction equation

HRID 1618928 reaction equation
[CH:1]1([CH2:4][NH:5][C:6]2[CH:11]=[CH:10][C:9](OC)=[CH:8][C:7]=2[N+:14]([O-])=O)[CH2:3][CH2:2]1.[CH2:17]([OH:19])C>>[CH:1]1([CH2:4][NH:5][C:6]2[C:7]([NH2:14])=[CH:8][CH:9]=[C:10]([O:19][CH3:17])[CH:11]=2)[CH2:2][CH2:3]1

Participants

3

Reactant 2

HCID 702EthanolHCID 29544554HCID 29544554, compound

Product 1

HCID 80457062HCID 80457062, compound

Conditions

Temperature
10 °C

Procedure

N-(Cyclopropylmethyl)-4-methoxy-2-nitroaniline (175 g) was dissolved in ethanol (1750 mL) and was added to a 4.0 L Hast ‘C” Shaker can. The mixture was cooled to 10° C. and treated with 3% Pt/0.6% VG/C, deGussa (4.5 g). The vessel was sparged under nitrogen and then sparged three times with hydrogen at a setting of 40 psi and agitated for 2.5 hours. To a pre-washed solka-flok with ethanol, the mixture was filtered through solka-flok through a sintered glass funnel to have about a ½ inch depth of solka-flok. The solka-flok was then washed with 1 L ethanol and concentrated in vacuo, providing the titled compound.

Workup

  1. additionwas added to a 4.0 L Hast ‘C” Shaker can
  2. customThe vessel was sparged under nitrogen
  3. customsparged three times with hydrogen at a setting of 40 psi
  4. filtrationTo a pre-washed solka-flok with ethanol, the mixture was filtered through solka-flok through a sintered glass funnel
  5. washThe solka-flok was then washed with 1 L ethanol
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-753b2038e266452cbd9b407d3febeab7
Source dataset
uspto-grants-2014_07
Patent number
US08772276B2

Reaction notes

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