Ammonium Chloride → HCID 67311109, compound

HRID 1930303Notes

Reaction equation

HRID 1930303 reaction equation
C1COCC1.C(O)C.[CH3:9][C:10]1[CH:15]=[CH:14][C:13]([N+:16]([O-])=O)=[CH:12][C:11]=1[CH2:19][C:20]([O:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[O:21].[Cl-].[NH4+]>C(OCC)(=O)C.[Cl-].[Na+].O.[Zn]>[NH2:16][C:13]1[CH:14]=[CH:15][C:10]([CH3:9])=[C:11]([CH2:19][C:20]([O:22][CH2:23][C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)=[O:21])[CH:12]=1

Participants

7

Reactant 3

HCID 25517Ammonium ChlorideHCID 21873804Tetrahydrofuran ethanolHCID 67311651HCID 67311651, compound

Product 1

HCID 67311109HCID 67311109, compound

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 8857Ethyl AcetateSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

In a solution of THF:ethanol (1:1, 100 mL) was placed the crude benzyl 2-(2-methyl-5-nitrophenyl)acetate (2.46 g, 8.62 mmol) and ammonium chloride (4.61 g, 86.2 mmol). To this was added zinc dust (5.64 g, 86.2 mmol) and the resulting slurry was stirred at RT for 4 hrs. The slurry was filtered through Celite and washed with ethanol (2×50 mL). The combined filtrates were evaporated at reduced pressure to give an oily mass. This was dissolved in a mixture of ethyl acetate (75 mL) and brine (75 mL). The organic phase dried (Na2SO4) and evaporated at reduced pressure to give benzyl 2-(5-amino-2-methylphenyl)acetate as an oil, which appears to be 6:4 mix of product:non-homologated compound. Used as is.

Workup

  1. filtrationThe slurry was filtered through Celite
  2. washwashed with ethanol (2×50 mL)
  3. customThe combined filtrates were evaporated at reduced pressure
  4. customto give an oily mass
  5. dry with materialThe organic phase dried (Na2SO4)
  6. customevaporated at reduced pressure

Sources & evidence

ORD record
ord-17e81e71cc284e87b88f81627ae827bd
Source dataset
uspto-grants-2012_05
Patent number
US08188113B2

Reaction notes

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