Hydrazine hydrate (1:1) → HCID 136378337, compound

HRID 1714835Notes

Reaction equation

HRID 1714835 reaction equation
[CH2:1]([C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[OH:13])[O:9][C:8]([C:14]([OH:16])=[O:15])=[C:7]([C:17]1[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=1)[C:6]2=O)[CH3:2].O.[NH2:27][NH2:28]>C(O)C>[CH2:1]([C:3]1[C:12]([OH:13])=[CH:11][C:10]([OH:9])=[C:5]([C:6]2[C:7]([C:17]3[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=3)=[C:8]([C:14]([OH:16])=[O:15])[NH:27][N:28]=2)[CH:4]=1)[CH3:2]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 68507470HCID 68507470, compound

Product 1

HCID 136378337HCID 136378337, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

6-Ethyl-7-hydroxy-3-(4-methoxyphenyl)-4-oxo-chromene-2-carboxylic acid (13.6 g, 41.73 mmol) and hydrazine monohydrate (6.1 ml, 125.19 mmol) were suspended in ethanol (200 ml) at room temperature. The mixture was then heated slowly to 70° C. and stirred at this temperature for 4 hours. The mixture was cooled to room temperature and all volatile components were removed in vacuum. The residue was partitioned between water (11) and Ethyl acetate (1.41). Then the aqueous phase was separated. The organic phase yielded some product. The remainder of the product was extracted from the aqueous phase with Ethyl acetate (4×500 ml). The combined organic extracts were dried over Magnesium sulfate and evaporated to dryness under vacuum resulting in a further quantity of the desired product. The combined isolated product portions yielded 6.99 g (51%) of a light brown solid. 1H NMR Spectrum: δH (400 MHz, DMSO-6d) 0.84 (3H t, J=7.5 Hz), 2.23 (2H q, J=7.5 Hz), 3.38 (1H s, br), 3.74 (3H, s), 6.36 (1H, s), 6.56 (1H, s), 6.85 (2H d, J=8.7 Hz), 7.13 (2H d, J=8.7 Hz), 9.3 (1H s, br), 9.4 (1H s, br), 12.8 (1H s, br); Mass Spectrum: (M+H+) 355.04, (M+H−) 353.09.

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. customall volatile components were removed in vacuum
  3. customThe residue was partitioned between water (11) and Ethyl acetate (1.41)
  4. customThen the aqueous phase was separated
  5. customThe organic phase yielded some product
  6. extractionThe remainder of the product was extracted from the aqueous phase with Ethyl acetate (4×500 ml)
  7. dry with materialThe combined organic extracts were dried over Magnesium sulfate
  8. customevaporated to dryness under vacuum

Sources & evidence

ORD record
ord-f2d904fd603245d6901738c1a81a3d2e
Source dataset
uspto-grants-2010_09
Patent number
US07799781B2

Reaction notes

Loading…