Hydrochloric Acid → HCID 4769382, compound

HRID 2273670Notes

Reaction equation

HRID 2273670 reaction equation
[OH-].[Na+].[C:3]([N:6]1[C:16]2[C:11](=[CH:12][C:13]([I:17])=[CH:14][CH:15]=2)[C:9](=O)[C:7]1=[O:8])(=[O:5])[CH3:4].N1C2C(=CC=CC=2)C=CC1=[O:28].Cl>O>[I:17][C:13]1[CH:12]=[C:11]2[C:16](=[CH:15][CH:14]=1)[NH:6][C:3](=[O:5])[CH:4]=[C:9]2[C:7]([OH:28])=[O:8]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 60382-HydroxyquinolineHCID 14798Sodium HydroxideHCID 3711542HCID 3711542, compound

Product 1

HCID 4769382HCID 4769382, compoundYield 36%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of sodium hydroxide (0.77 g, 19.3 mmol) in water (46.5 mL), was added N-acetyl-5-iodoisatine (107) (2.50 g, 7.86 mmol) (Aeschlimann, J. A. The relative stability of the quinolone and indolinone rings. J. Chem. Soc. 1926, 2908). The mixture was refluxed for 3 h. After cooling to room temperature and then 0° C., a 6 N aqueous hydrochloric acid solution was added (pH=1). The precipitate was filtered and suspended in a saturated aqueous sodium bicarbonate solution (10 mL). The remaining precipitate was filtered and the filtrate was extracted with dichloromethane (6×50 mL). The aqueous layer was acidified up to pH=1 with a 6 N aqueous hydrochloric acid solution and left 1 h at 0° C. The precipitate formed was filtered and dried under vacuum at 35° C. to give compound 108 (0.90 g, 2.86 mmol) as an ocher solid. Yield 36%; mp 361-363° C.; IR (KBr) ν 1219, 1636, 1701, 2800-3150, 3200-3500 cm−1; 1H NMR (200 MHz, DMSO-d6) δ 6.92 (s, 1H), 7.18 (d, 1H, J=8.7 Hz), 7.84 (dd, 1H, J=1.8, 8.7 Hz), 8.57 (d, 1H, J=1.8 Hz), 12.17 (s, 1H), 14.00 (m, 1H); ESI-MS m/z 313.7 [M−H].

Workup

  1. temperatureThe mixture was refluxed for 3 h
  2. filtrationThe precipitate was filtered
  3. filtrationThe remaining precipitate was filtered
  4. extractionthe filtrate was extracted with dichloromethane (6×50 mL)
  5. customThe precipitate formed
  6. filtrationwas filtered
  7. customdried under vacuum at 35° C.

Sources & evidence

ORD record
ord-1492ba26a1fb4bdea4d45e93f334d948
Source dataset
uspto-grants-2015_09
Patent number
US09125937B2

Reaction notes

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