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

HRID 970351Notes

Reaction equation

HRID 970351 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 (3X's) and the ethyl acetate washed with water (3X'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=10.92.8 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 (3X's)
  2. washthe ethyl acetate washed with water (3X'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-599a310c7baf4ef68b1f12af255b691c
Source dataset
uspto-grants-2007_12
Patent number
US07312215B2

Reaction notes

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