Methanol → HCID 22478631, compound

HRID 736506Notes

Reaction equation

HRID 736506 reaction equation
[CH3:1][NH:2][C:3]1[S:4][C:5]2[CH:11]=[CH:10][C:9]([N+:12]([O-])=O)=[CH:8][C:6]=2[N:7]=1.Cl[Sn]Cl.CO.O>C1COCC1.C(OCC)(=O)C>[CH3:1][NH:2][C:3]1[S:4][C:5]2[CH:11]=[CH:10][C:9]([NH2:12])=[CH:8][C:6]=2[N:7]=1

Participants

7

Reactant 4

HCID 887MethanolHCID 962WaterHCID 24479Stannous ChlorideHCID 22478944HCID 22478944, compound

Product 1

HCID 22478631HCID 22478631, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of nitro compound 456a (593 mg; 2.83 mmol); SnCl2 (4.02 g; 20.8 mmol; 7.35 eq) and NH4OAc (4.5g) was suspended in THF:MeOH:H2O=1:1:1 (60 mL) and stirred at 70° C. for 2 h, cooled down, diluted with ethyl acetate and successively washed with saturated NaHCO3 and brine; dried (MgSO4) filtered and concentrated. The residue (443 mg; 2.43 mmol; 87%) showed consistent spectrum and suitable purity degree for synthetic purposes, therefore was submitted to the next step without further purification.

Workup

  1. temperaturecooled down
  2. washsuccessively washed with saturated NaHCO3 and brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customwas submitted to the next step without further purification

Sources & evidence

ORD record
ord-f66df002e2c74b02bc9285b131559b95
Source dataset
uspto-grants-2009_09
Patent number
US07595343B2

Reaction notes

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