Ethanol → Ethyl 3-amino-5-bromobenzoate

HRID 2208689Notes

Reaction equation

HRID 2208689 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([N+:12]([O-])=O)[CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].[NH4+].[Cl-].[CH2:17](O)C>C(=O)(O)[O-].[Na+].[Fe]>[NH2:12][C:10]1[CH:9]=[C:4]([CH:3]=[C:2]([Br:1])[CH:11]=1)[C:5]([O:7][CH2:8][CH3:17])=[O:6]

Participants

6

Reactant 3

HCID 702EthanolHCID 25517Ammonium ChlorideHCID 239341Methyl 3-bromo-5-nitrobenzoate

Product 1

HCID 63021768Ethyl 3-amino-5-bromobenzoateYield 99.14%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
90 °C

Procedure

To a stirred solution of methyl 3-bromo-5-nitrobenzoate (17 g, 62.04 mmol) in ethanol (85 mL), was added NH4Cl solution (17 g in 85 mL water, 317.8 mmol) followed by Fe powder (27.82 g, 498.12 mmol). Resulting reaction mass was stirred at 90° C. for 1 h. On completion, reaction mass was filtered and filtrate concentrated till dryness to get solid which was dissolved in sat. sodium bicarbonate solution. Aqueous layer was extracted with ethyl acetate (3×50 mL). Combined organic layers were dried over sodium sulfate and concentrated to afford the desired compound (15 g, 99.14%).

Workup

  1. customResulting
  2. customreaction mass
  3. customOn completion, reaction mass
  4. filtrationwas filtered
  5. concentrationfiltrate concentrated till dryness
  6. customto get solid which
  7. extractionAqueous layer was extracted with ethyl acetate (3×50 mL)
  8. dry with materialCombined organic layers were dried over sodium sulfate
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-d8a9ca86fb9f485391699a8de7ed255e
Source dataset
uspto-grants-2016_06
Patent number
US09376422B2

Reaction notes

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