Water → HCID 13288075, compound

HRID 1903907Notes

Reaction equation

HRID 1903907 reaction equation
COC([CH2:5][NH:6][N:7]1[C:16]2[CH:15]=[C:14]3[O:17][CH2:18][O:19][C:13]3=[CH:12][C:11]=2[C:10](=[O:20])[C:9]([C:21]([O:23]CC)=[O:22])=[CH:8]1)=O.[OH-].[Na+].O>C(O)(=O)C>[CH3:5][NH:6][N:7]1[C:16]2[CH:15]=[C:14]3[O:17][CH2:18][O:19][C:13]3=[CH:12][C:11]=2[C:10](=[O:20])[C:9]([C:21]([OH:23])=[O:22])=[CH:8]1

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 57088283HCID 57088283, compound

Product 1

HCID 13288075HCID 13288075, compoundYield 86.7%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
95 °C

Procedure

A mixture of 4.6 g (0.0132 mole) of ethyl 5,8-dihydro-5-[(methoxycarbonyl)methylamino]-8-oxo-1,3-dioxolo[4,5-g]-quinoline-7-carboxylate (Example 5), 1.6 g (0.0396 mole) of sodium hydroxide and about 100 ml of water was stirred at 95° C. for 4.5 hours. The reaction mixture was cooled, acidified with 5 ml of acetic acid with stirring, and kept in a refrigerator overnight. The solid product was collected by filtration, washed with water and recrystallized from 70 ml of boiling dimethylformamide. There was obtained 3 g of 5,8-dihydro-5-(methylamino)-8-oxo-1,3-dioxolo[4,5-g]quinoline-7-carboxylic acid, colorless crystals, m.p. above 300° C.

Workup

  1. temperatureThe reaction mixture was cooled
  2. stirringwith stirring
  3. customkept in a refrigerator overnight
  4. filtrationThe solid product was collected by filtration
  5. washwashed with water
  6. customrecrystallized from 70 ml of boiling dimethylformamide

Sources & evidence

ORD record
ord-61701e361e614368b03102af5c86aba8
Source dataset
uspto-grants-1984_03
Patent number
US04439436

Reaction notes

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