Lithium hydroxide, monohydrate → 2-Fluoro-5-phenylamino-terephthalic Acid

HRID 970328Notes

Reaction equation

HRID 970328 reaction equation
C[O:2][C:3](=[O:22])[C:4]1[CH:13]=[C:12]([NH:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:7]([C:8]([O:10]C)=[O:9])=[CH:6][C:5]=1[F:21].O.[OH-].[Li+]>CO.C1COCC1.O>[F:21][C:5]1[CH:6]=[C:7]([C:8]([OH:10])=[O:9])[C:12]([NH:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:13][C:4]=1[C:3]([OH:22])=[O:2]

Participants

6

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 167486382-Fluoro-5-phenylamino-terephthalic Acid Dimethyl Ester

Product 1

HCID 167483932-Fluoro-5-phenylamino-terephthalic Acid

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
75 °C

Procedure

A mixture of 174C (30.0 g, 9.89 mmol) and lithium hydroxide monohydrate (12.5 g, 29.7 mmol) in MeOH (200 mL), THF (200 mL) and water (100 mL) was heated at 75° C. for 0.5 h. HPLC indicated that the reaction was complete. The organic solvents were removed under reduced pressure, and the aqueous residue was diluted with water. The pH was adjusted to 3.0 with 6N aqueous hydrochloric acid which resulted in a precipitate. The solid was collected by vacuum filtration and dried under reduced pressure to provide a quantitative yeild of compound 174D as an orange-yellow solid. HPLC retention time=3.02 min. (Condition B). 1H-NMR (400 MHz, DMSO) δ7.11 (m, 1H), 7.25 (m, 2H), 7.39 (m, 2H), 7.60 (m, 1H), 7.68 (m, 1H), 9.32 (br s, 1H), and 13.55 (br s, 2H).

Workup

  1. customThe organic solvents were removed under reduced pressure
  2. additionthe aqueous residue was diluted with water
  3. customresulted in a precipitate
  4. filtrationThe solid was collected by vacuum filtration
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-519e0b01bc1a47d38ac86c01f9ec3bc8
Source dataset
uspto-grants-2007_12
Patent number
US07312209B2

Reaction notes

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