Hydrochloric Acid → HCID 86657977, compound

HRID 2366807Notes

Reaction equation

HRID 2366807 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:18])[O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:4][C:3]=1[O:19][C:20]1[CH:25]=[CH:24][C:23]([N+:26]([O-])=O)=[CH:22][N:21]=1.CN1CCCC1=O.Cl>C(O)C.C(OCC)(=O)C.[OH-].[Na+]>[NH2:26][C:23]1[CH:24]=[CH:25][C:20]([O:19][C:3]2[CH:4]=[C:5]([NH:8][C:9](=[O:18])[O:10][CH2:11][C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH:6]=[CH:7][C:2]=2[CH3:1])=[N:21][CH:22]=1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 13387N-methyl-2-pyrrolidoneHCID 86657976HCID 86657976, compound2×

Product 1

HCID 86657977HCID 86657977, compoundYield 166.3%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolventHCID 14798Sodium HydroxideSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of benzyl {4-methyl-3-[(5-nitropyridin-2-yl)oxy]phenyl}carbamate (36.9 g, 97.4 mmol) in ethanol (200 mL)/1-methylpyrrolidin-2-one (50 mL) were added 1N hydrochloric acid (50 mL) and reduced iron (27.2 g, 487 mmol), and the mixture was stirred at 100° C. for 3 hr. The reaction mixture was diluted with ethyl acetate (200 mL), and 2N aqueous sodium hydroxide solution (50 mL) was added. The insoluble material was filtered off through a celite pad, and the insoluble material was washed with ethyl acetate (1 L). Benzyl {4-methyl-3-[(5-nitropyridin-2-yl)oxy]phenyl}carbamate (38.3 g, 101 mmol) was treated in the same manner as above. The obtained filtrates were combined, washed with saturated brine (3×200 mL), and purified by silica gel (ethyl acetate). The obtained solution was concentrated under reduced pressure, and the crystals precipitated during concentration were collected by filtration to give the title compound (56.6 g, 82%) as a pale-orange solid.

Workup

  1. additionwas added
  2. filtrationThe insoluble material was filtered off through a celite pad
  3. washthe insoluble material was washed with ethyl acetate (1 L)
  4. washwashed with saturated brine (3×200 mL)
  5. custompurified by silica gel (ethyl acetate)
  6. concentrationThe obtained solution was concentrated under reduced pressure
  7. customthe crystals precipitated during concentration
  8. filtrationwere collected by filtration

Sources & evidence

ORD record
ord-635be7edc63a4b60ab165045624a7c6b
Source dataset
uspto-grants-2014_04
Patent number
US08697874B2

Reaction notes

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