Acetic Acid → HCID 18690998, compound

HRID 1184919Notes

Reaction equation

HRID 1184919 reaction equation
[CH3:1][C:2]1[CH:12]=[CH:11][C:10]([N+:13]([O-])=O)=[CH:9][C:3]=1[C:4]([O:6][CH2:7][CH3:8])=[O:5].C(O)(=O)C>C1COCC1.[Zn]>[NH2:13][C:10]1[CH:11]=[CH:12][C:2]([CH3:1])=[C:3]([CH:9]=1)[C:4]([O:6][CH2:7][CH3:8])=[O:5]

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 18510875Ethyl 2-methyl-5-nitrobenzoate

Product 1

HCID 18690998HCID 18690998, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 2-methyl-5-nitrobenzoate 101 and acetic acid (516 mmol, 29.6 mL) (25.8 mmol, 5.4 g) in THF (129 mL) at 0° C. was added zinc (516 mmol, 33.8 g) and stirred for 1 h. The reaction was filtered, neutralized with 2N NaOH solution and extracted with ethyl acetate (2×). Organic layers were washed with water, brine, dried and concentrated under reduced pressure to give ethyl 5-amino-2-methylbenzoate 102 (4.6 g, 100%).

Workup

  1. filtrationThe reaction was filtered
  2. extractionextracted with ethyl acetate (2×)
  3. washOrganic layers were washed with water, brine
  4. customdried
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-57ff3eef873149cb8d742a172643647e
Source dataset
uspto-grants-2014_03
Patent number
US08669256B2

Reaction notes

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