Hydrochloric Acid → HCID 58575185, compound

HRID 1807844Notes

Reaction equation

HRID 1807844 reaction equation
C([NH:5][C:6]1[C:15]([N+:16]([O-:18])=[O:17])=[CH:14][C:9]([C:10]([O:12][CH3:13])=[O:11])=[C:8]([CH2:19][O:20][CH3:21])[CH:7]=1)(C)(C)C.Cl>CO>[NH2:5][C:6]1[C:15]([N+:16]([O-:18])=[O:17])=[CH:14][C:9]([C:10]([O:12][CH3:13])=[O:11])=[C:8]([CH2:19][O:20][CH3:21])[CH:7]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 67134197HCID 67134197, compound

Product 1

HCID 58575185HCID 58575185, compoundYield 85.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a mixed liquid of 6.80 g of methyl 4-(tert-butylamino)-2-(methoxymethyl)-5-nitrobenzoate and 68.0 mL of methanol was added 37.0 mL of 6 M hydrochloric acid, followed by stirring overnight under the heating and refluxing condition. The solvent was evaporated under reduced pressure, and then 111 mL of methanol and 1.00 mL of concentrated sulfuric acid were added thereto, followed by stirring overnight under the heating and refluxing condition. Ethyl acetate and a saturated aqueous sodium hydrogen carbonate solution were added thereto, followed by extraction with ethyl acetate, the organic layer was washed with saturated brine and then dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure to obtain 4.73 g of methyl 4-amino-2-(methoxymethyl)-5-nitrobenzoate as a yellow solid.

Workup

  1. temperaturerefluxing condition
  2. customThe solvent was evaporated under reduced pressure
  3. addition111 mL of methanol and 1.00 mL of concentrated sulfuric acid were added
  4. stirringby stirring overnight under the heating and
  5. temperaturerefluxing condition
  6. additionEthyl acetate and a saturated aqueous sodium hydrogen carbonate solution were added
  7. extractionfollowed by extraction with ethyl acetate
  8. washthe organic layer was washed with saturated brine
  9. dry with materialdried over anhydrous magnesium sulfate
  10. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-9f8a5c1fcd6646fe94a4750d7e8279d5
Source dataset
uspto-grants-2013_01
Patent number
US08357688B2

Reaction notes

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