HCID 57605189, compound → HCID 10384506, compound

HRID 1882330Notes

Reaction equation

HRID 1882330 reaction equation
C[O:2][C:3](=[O:29])[CH2:4][O:5][C:6]1[CH:15]=[C:14]2[C:9]([C:10](=[O:28])[C:11]([C:16]3[CH:21]=[CH:20][C:19]([O:22][CH2:23][C:24]([O:26]C)=[O:25])=[CH:18][CH:17]=3)=[CH:12][O:13]2)=[CH:8][CH:7]=1>Cl>[C:24]([CH2:23][O:22][C:19]1[CH:18]=[CH:17][C:16]([C:11]2[C:10](=[O:28])[C:9]3[C:14](=[CH:15][C:6]([O:5][CH2:4][C:3]([OH:29])=[O:2])=[CH:7][CH:8]=3)[O:13][CH:12]=2)=[CH:21][CH:20]=1)([OH:26])=[O:25]

Participants

3

Reactant 1

HCID 57605189HCID 57605189, compound

Product 1

HCID 10384506HCID 10384506, compoundYield 86.1%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Conditions

Temperature
90 °C

Procedure

To mixture of [3-(4-Methoxycarbonylmethoxy-phenyl)-4-oxo-4H-chromen-7-yloxy]-acetic acid methyl ester 52 (45 grams, 113.5 mmol) and concentrated hydrochloric acid (250 mL) was heated at 90° C. for 5 hours. The reaction mixture was cooled to room temperature and poured onto ice water (250 mL), filtered the solids, washed with water, methanol and dried. Crude 97 was recrystallized from Dimethyl formamide and Precipitated with water to give pure 97 (36 grams, 86.1%) as a white powder. M.p: 270-272.2° C.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. additionpoured onto ice water (250 mL)
  3. filtrationfiltered the solids
  4. washwashed with water, methanol
  5. customdried
  6. customCrude 97 was recrystallized from Dimethyl formamide
  7. customPrecipitated with water

Sources & evidence

ORD record
ord-937e2df29cd14ed6b34e399fd7f33797
Source dataset
uspto-grants-2012_11
Patent number
US08318973B2

Reaction notes

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