4-[5-(4-Chloro-phenyl)-[1,3,4]oxadiazol-2-yl]-2-nitro-phenylamine → 4-[5-(4-Chloro-phenyl)-[1,3,4]oxadiazol-2-yl]-benzene-1,2-diamine

HRID 1360739Notes

Reaction equation

HRID 1360739 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:12][C:11]([C:13]3[CH:18]=[CH:17][C:16]([NH2:19])=[C:15]([N+:20]([O-])=O)[CH:14]=3)=[N:10][N:9]=2)=[CH:4][CH:3]=1>C1COCC1.CCO>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[O:12][C:11]([C:13]3[CH:14]=[C:15]([NH2:20])[C:16]([NH2:19])=[CH:17][CH:18]=3)=[N:10][N:9]=2)=[CH:6][CH:7]=1

Participants

3

Reactant 1

HCID 669656894-[5-(4-Chloro-phenyl)-[1,3,4]oxadiazol-2-yl]-2-nitro-phenylamine

Product 1

HCID 669664354-[5-(4-Chloro-phenyl)-[1,3,4]oxadiazol-2-yl]-benzene-1,2-diamine

Reagents, catalysts & solvents 1

HCID 21873804Tetrahydrofuran ethanolSolvent

Procedure

To a 25 mL rbf was added 0.4137 g (1.31 mmol) of 4-[5-(4-Chloro-phenyl)-[1,3,4]oxadiazol-2-yl]-2-nitro-phenylamine, 4 mL of THF/EtOH (1:1). Vacuum flushed 3×, then added 0.1655 g of PtO2 (40% by weight) as a slurry in 2 mL of THF/EtOH (1:1). It was flushed with H2 3× and allowed to stir at r.t. for 18 h. 10 ml DCM and Celite was added and it was let stir 1 h. The mixture was then filtered through Celite pad, and the filter cake was rinsed with 20 mL DCM. The filtrate was reduced in vacuo to give the title compound. 1H NMR (400 MHz, DMSO-d6) δ ppm 4.85 (br. s., 1.7H) 5.31 (br. s., 1.7H) 6.62 (d, J=8.08 Hz, 1H) 7.19 (dd, J=8.08, 1.89 Hz, 1H) 7.26 (d, J=2.02 Hz, 1H) 7.66-7.70 (m, 2H) 8.02-8.06 (m, 2H). MS (m/z) 287.2 M (+1), tR=1.18, Meth 10

Workup

  1. customVacuum flushed 3×
  2. additionadded 0.1655 g of PtO2 (40% by weight) as a slurry in 2 mL of THF/EtOH (1:1)
  3. customIt was flushed with H2 3×
  4. addition10 ml DCM and Celite was added
  5. stirringit was let stir 1 h
  6. filtrationThe mixture was then filtered through Celite pad
  7. washthe filter cake was rinsed with 20 mL DCM

Sources & evidence

ORD record
ord-2d31942512ce4d9682805db9c03526db
Source dataset
uspto-grants-2011_02
Patent number
US07879850B2

Reaction notes

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