Ammonium Chloride → 2-Ethoxy-4-aminobenzoic acid

HRID 2263949

Reaction equation

HRID 2263949 reaction equation
[CH2:1]([O:3][C:4]1[CH:12]=[C:11]([N+:13]([O-])=O)[CH:10]=[CH:9][C:5]=1[C:6]([OH:8])=[O:7])[CH3:2].[Cl-].[NH4+]>C(O)C.[Fe]>[NH2:13][C:11]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[C:4]([O:3][CH2:1][CH3:2])[CH:12]=1

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 27363472-Ethoxy-4-nitrobenzoic acid

Product 1

HCID 101763852-Ethoxy-4-aminobenzoic acidYield 88.1%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

2-Ethoxy-4-nitrobenzoic acid (20 g, 94 mmol, Aldrich) was suspended in ethanol (170 mL) and combined with a saturated aqueous solution of ammonium chloride (100 mL). As this was rapidly stirred, iron dust (13.3 g, 239 mmol) was added in portions. The temperature was raised to 80° C. for 1 h. The cooled suspension was filtered through Celite, and the cake washed with dichloromethane (150 mL). The filtrate was diluted with dichloromethane and washed with brine, dried over magnesium sulfate, filtered and evaporated. A brown solid was triturated with dichloromethane and filtered to give 15 g of 4-amino-2-ethoxybenzoic acid (88%).

Workup

  1. filtrationThe cooled suspension was filtered through Celite
  2. washthe cake washed with dichloromethane (150 mL)
  3. additionThe filtrate was diluted with dichloromethane
  4. washwashed with brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. customA brown solid was triturated with dichloromethane
  9. filtrationfiltered

Sources & evidence

ORD record
ord-6840192751e7404f86f9691611b22422
Source dataset
uspto-grants-2010_12
Patent number
US07851626B2

Linked notes

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