Water → HCID 178515552, compound

HRID 1161604Notes

Reaction equation

HRID 1161604 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:8]1[CH:13]=[CH:12][C:11](N)=[CH:10][CH:9]=1.Cl.[OH2:16].[OH-].[Na+].[C:19]1([CH3:25])C=CC=C[CH:20]=1>>[C:11]1([C:25]2[CH:19]=[C:20]([OH:16])[C:7]3[C:2](=[CH:3][CH:4]=[CH:5][CH:6]=3)[N:1]=2)[CH:12]=[CH:13][CH:8]=[CH:9][CH:10]=1

Participants

6

Reactant 5

HCID 962WaterHCID 1140TolueneHCID 6115AnilineHCID 8870Benzenamine hydrochloride (1:1)HCID 14798Sodium Hydroxide

Product 1

HCID 178515552HCID 178515552, compoundYield 20%

Conditions

Temperature
135 °C

Procedure

This amide (250 mg, 1.53 mmol) was refluxed using a Dean-Stark apparatus with aniline (143 mg, 1.53 mmol) and aniline.HCl (10 mg, 0.08 mmol) in toluene (10 mL) for 16 h. The solution was concentrated to afford a brown oil that was mixed with polyphosphoric acid (2 g) and heated at 135° C. for 20 min. The reaction mixture was poured into water and adjusted to pH 8 with 5 M NaOH. The aqueous suspension was extracted twice with ethyl acetate. The organic layers were combined, washed with brine, dried over MgSO4, filtered and concentrated. The residue was flash chromatographed on silica gel, eluting with 3% MeOH in ethyl acetate, to give 2-phenyl-4-hydroxyquinoline (2), 67 mg, 20% yield.

Workup

  1. customfor 16 h
  2. concentrationThe solution was concentrated
  3. customto afford a brown oil that
  4. extractionThe aqueous suspension was extracted twice with ethyl acetate
  5. washwashed with brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customchromatographed on silica gel
  10. washeluting with 3% MeOH in ethyl acetate

Sources & evidence

ORD record
ord-6841736f1a02415e9282e09611e7b864
Source dataset
uspto-grants-2010_10
Patent number
USRE041894E1

Reaction notes

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