HCID 29544554, compound → HCID 70197765, compound

HRID 2281032Notes

Reaction equation

HRID 2281032 reaction equation
[CH:1]1([CH2:4][NH:5][C:6]2[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[CH:8][C:7]=2[N+:14]([O-])=O)[CH2:3][CH2:2]1>C(O)C>[CH:1]1([CH2:4][NH:5][C:6]2[C:7]([NH2:14])=[CH:8][C:9]([O:12][CH3:13])=[CH:10][CH:11]=2)[CH2:2][CH2:3]1

Participants

3

Reactant 1

HCID 29544554HCID 29544554, compound

Product 1

HCID 70197765HCID 70197765, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
10 °C

Procedure

N-(Cyclopropylmethyl)-4-methoxy-2-nitroaniline (175 g) was dissolved in ethanol (1750 mL) and 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. additionadded 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-253a7fc29a8e4fb1a81edc5982dcceab
Source dataset
uspto-grants-2015_09
Patent number
US09139576B2

Reaction notes

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