Water → 3-Amino-5-fluoro-2-nitro phenyl acetic acid

HRID 1793718Notes

Reaction equation

HRID 1793718 reaction equation
C([O:5][C:6](=[O:26])[CH:7]([C:15]1[CH:20]=[C:19]([F:21])[CH:18]=[C:17]([NH2:22])[C:16]=1[N+:23]([O-:25])=[O:24])C(OC(C)(C)C)=O)(C)(C)C.O>Cl.O1CCOCC1>[NH2:22][C:17]1[C:16]([N+:23]([O-:25])=[O:24])=[C:15]([CH2:7][C:6]([OH:26])=[O:5])[CH:20]=[C:19]([F:21])[CH:18]=1

Participants

5

Reactant 2

HCID 962WaterHCID 235418872-(3-Amino-5-fluoro-2-nitro-phenyl)-malonic acid di-tert-butyl ester

Product 1

HCID 235416553-Amino-5-fluoro-2-nitro phenyl acetic acid

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
40 °C

Procedure

To the 2-(3-Amino-5-fluoro-2-nitro-phenyl)-malonic acid di-tert-butyl ester (140 g) in 500 mL of 4N HCl in dioxane was added 50 mL of water and heated to 40° C. for 2 days. The solution was extracted with ethyl acetate (3×'s) and the ethyl acetate washed with water (3×'s) and brine. The organic fraction was dried over MgSO4 and was concentrated to give 78 g of crude (66% pure by LC/MS); 1H NMR (500 MHz, DMSO) δ 12.40 (brs, 1H), 7.04 (s, 2H), 6.68 (dd, J=10.9 2.8 Hz, 1H), 6.47 (dd, J=10.9, 2.8 Hz, 1H), 3.80 (s, 2H).

Workup

  1. extractionThe solution was extracted with ethyl acetate (3×'s) and the ethyl acetate
  2. washwashed with water (3×'s) and brine
  3. dry with materialThe organic fraction was dried over MgSO4
  4. concentrationwas concentrated
  5. customto give 78 g of crude (66% pure by LC/MS)

Sources & evidence

ORD record
ord-ae98883c29bc486cb8fa1214b299bb7a
Source dataset
uspto-grants-2006_07
Patent number
US07081454B2

Reaction notes

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