Toluene → HCID 13505096, compound

HRID 746085Notes

Reaction equation

HRID 746085 reaction equation
[CH3:1][C:2]1[C:7]([Cl:8])=[C:6]([O:9][C:10]2[CH:15]=[CH:14][C:13]([C:16](=[O:24])[C:17]3[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=3)=[CH:12][CH:11]=2)[C:5]([CH3:25])=[CH:4][C:3]=1[N+:26]([O-])=O.C1(C)C=CC=CC=1.C(Cl)(Cl)Cl>[Pt].C(OCC)(=O)C.CCCCCC>[CH3:1][C:2]1[C:7]([Cl:8])=[C:6]([O:9][C:10]2[CH:11]=[CH:12][C:13]([C:16](=[O:24])[C:17]3[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=3)=[CH:14][CH:15]=2)[C:5]([CH3:25])=[CH:4][C:3]=1[NH2:26]

Participants

7

Reactant 3

HCID 1140TolueneHCID 6212ChloroformHCID 13656005HCID 13656005, compound

Product 1

HCID 13505096HCID 13505096, compound

Reagents, catalysts & solvents 3

HCID 23939PlatinumCatalystHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 2,5-dimethyl-3-chloro-4-(4-[4-chlorobenzoyl]phenoxy)nitrobenzene (5.95 g, 14 mmol), toluene (160 mL), and 5% platinum on carbon (0.65 g) was subjected to hydrogenation at the pressure ≤24 psi. After 8 h one reaction was found to be partly completed. Additional catalyst (0.2 g of 5% pt/c) was added. The reaction was close to completion by the end of additional 4 h. The mixture was filtered and the filtrate was concentrated to give an amber foam. This foam was dissolved in an ethyl acetate (5 mL) and hexane (10 mL). Solid formed after the addition of seed crystal and vigorous stirring. A tan powder was obtained after filtration (3.93 g); mp 113°-122°. In a similar experiment a buff powder was obtained; IR (CHCl3) 3020, 2405, 1650, 1600 cm-1 ; NMR (CDCl3) δ 6.6-7.8 (M, 8H), 6.5 (S, 1H) 3.5 (br, 2H), 2.2 (S, 3H), 2.1 (S, 3H)

Workup

  1. customAfter 8 h one reaction
  2. additionAdditional catalyst (0.2 g of 5% pt/c) was added
  3. customThe reaction was close to completion by the end of additional 4 h
  4. filtrationThe mixture was filtered
  5. concentrationthe filtrate was concentrated
  6. customto give an amber foam
  7. customSolid formed
  8. additionafter the addition of seed crystal and vigorous stirring
  9. customA tan powder was obtained
  10. filtrationafter filtration (3.93 g)
  11. customIn a similar experiment a buff powder was obtained

Sources & evidence

ORD record
ord-ed02e69d169c47ca92d4f65649d8c588
Source dataset
uspto-grants-1986_07
Patent number
US04602109

Reaction notes

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