HCID 10757002, compound → HCID 10398374, compound

HRID 2258556Notes

Reaction equation

HRID 2258556 reaction equation
C([O:8][C:9]1[C:17]([Cl:18])=[C:16]([CH3:19])[C:15]([CH3:20])=[C:11]([C:12]([OH:14])=[O:13])[C:10]=1[NH2:21])C1C=CC=CC=1>CCO.[Pd]>[Cl:18][C:17]1[C:9]([OH:8])=[C:10]([NH2:21])[C:11](=[C:15]([CH3:20])[C:16]=1[CH3:19])[C:12]([OH:14])=[O:13]

Participants

4

Reactant 1

HCID 10757002HCID 10757002, compound

Product 1

HCID 10398374HCID 10398374, compoundYield 46.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

3-Benzyloxy-4-chloro-5,6-dimethylanthranilic acid (10 mg, 0.03 mmol) was dissolved in EtOH (1.5 mL) and 10% Pd/C (2 mg) was added. Hydrogenation at room temperature and atmospheric pressure for 5 h, filtration, evaporation yielded 7 mg of crude product. Purification by preparative HPLC (Lichrosorb-C18, MeOH-Phosphate buffer (pH3) 50:50) adjusting the pH to 5 with NaHCO3 (aq), concentrating by a stream of N2, extracting with EtOAc (3×5 mL), washing the organic phase with brine, drying (MgSO4) and evaporating afforded the title compound (3 mg). 1H NMR (DMSO-d6): δ 3.3 (br, OH), 3.16 (s, 2 H), 2.16 (s, 3 H), 2.15 (s, 3 H); 13C NMR (DMSO-d6): δ 169.92, 137.87, 135.16, 126.38, 123.51, 121.39, 117.31, 17.72, 15.95; MS (EI, 70 eV): m/z (rel.int.) 217/215 (M+, 21/63),199/197 (20/59), 171/169 (37/100).

Workup

  1. filtrationfiltration, evaporation
  2. customyielded 7 mg of crude product
  3. customPurification by preparative HPLC (Lichrosorb-C18, MeOH-Phosphate buffer (pH3) 50:50)
  4. concentrationconcentrating by a stream of N2
  5. extractionextracting with EtOAc (3×5 mL)
  6. washwashing the organic phase with brine
  7. dry with materialdrying (MgSO4)
  8. customevaporating

Sources & evidence

ORD record
ord-25341416ff7a40c295419423524f8ddd
Source dataset
uspto-grants-1997_08
Patent number
US05661183

Reaction notes

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