HCID 86689280, compound → HCID 86689281, compound

HRID 537289Notes

Reaction equation

HRID 537289 reaction equation
[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11](=[O:23])[CH2:12][O:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([O:20][CH2:21][CH3:22])[CH:15]=2)=[C:6]([N+:24]([O-])=O)[CH:5]=1)[CH3:2]>[Pd].CCOC(C)=O>[NH2:24][C:6]1[CH:5]=[C:4]([O:3][CH2:1][CH3:2])[CH:9]=[CH:8][C:7]=1[NH:10][C:11](=[O:23])[CH2:12][O:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([O:20][CH2:21][CH3:22])[CH:15]=1

Participants

4

Reactant 1

HCID 86689280HCID 86689280, compound

Product 1

HCID 86689281HCID 86689281, compoundYield 100.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A 350 mL hydrogenation vessel was charged with nitroarene 48a (14.2 g, 39.4 mmol) and EtOAc (150 mL). To the resultant suspension was added 10% Pd/C (1.5 g). The mixture was hydrogenated on a Parr shaker at 58 psi overnight. The catalyst was filtered off on glass fiber paper and rinsed with EtOAc (75 mL). The filtrate was concentrated in vacuo to give 13.1 g of 49a as a white solid (100%). 1H NMR (300 MHz, CDCl3): δ 8.01 (s, 1H), 7.27 (d, 1H), 7.24 (d, 1H), 7.08 (d, 1H), 6.63-6.55 (m, 3H), 6.40-3.32 (m, 2H), 4.64 (s, 2H), 4.04 (qt, 2H), 3.99 (qt, 2H), 3.82 (bs, 2H), 1.44 (t, 3H), 1.41 (t, 3H) ppm. HPLC analysis (10:10:80 H2O:A1:MeOH) showed a purity of 98% with a retention time of 3.7 min.

Workup

  1. customwas hydrogenated on a Parr shaker at 58 psi overnight
  2. filtrationThe catalyst was filtered off on glass fiber paper
  3. washrinsed with EtOAc (75 mL)
  4. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-9cb2e5163bf2432aa5bde8148af1d0fd
Source dataset
uspto-grants-2014_10
Patent number
US08859780B2

Reaction notes

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