Hydrochloric Acid → HCID 86656184, compound

HRID 1192700Notes

Reaction equation

HRID 1192700 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:20]([O:22]C)=O)[C:5]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([F:19])[CH:14]=2)=[C:6]([N+:10]([O-:12])=[O:11])[C:7]=1[C:8]#N.[H-].C([Al+]CC(C)C)C(C)C.CCCCCC.Cl.[OH2:41]>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:20][OH:22])[C:5]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([F:19])[CH:14]=2)=[C:6]([N+:10]([O-:12])=[O:11])[C:7]=1[CH:8]=[O:41]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 962WaterHCID 8058HexaneHCID 21225700DiisobutylaluminumhydrideHCID 86656183HCID 86656183, compound

Product 1

HCID 86656184HCID 86656184, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of methyl 4-chloro-5-cyano-3′-fluoro-6-nitrobiphenyl-2-carboxylate (1.02 g, 3.05 mmol) in methylene chloride (20 mL) was added 1.0 M diisobutylaluminum hydride in hexane (7.6 mL, 7.6 mmol) at −78° C. The reaction was warmed to room temperature over 2 hours with stirring. 5.0 M Hydrogen chloride in water (30 mL, 100 mmol) was slowly added with stirring for 1 hour. The resulting mixture was extracted with ethyl acetate. The combined organic layers were washed with brine, dried over sodium sulfate and then concentrated to dryness. The residue was purified on silica gel, eluting with 0 to 50% ethyl acetate in hexane, to give the desired product (0.50 g, 53%). LCMS calculated for C14H10ClFNO4 (M+H)+: m/z=310.0; Found: 310.0.

Workup

  1. stirringwith stirring for 1 hour
  2. extractionThe resulting mixture was extracted with ethyl acetate
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated to dryness
  6. customThe residue was purified on silica gel
  7. washeluting with 0 to 50% ethyl acetate in hexane

Sources & evidence

ORD record
ord-270dc44e2f8b4a1cbffd9d9da5de3a6a
Source dataset
uspto-grants-2014_03
Patent number
US08680108B2

Reaction notes

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