Ethanol → HCID 54710199, compound

HRID 1598547Notes

Reaction equation

HRID 1598547 reaction equation
C([O:3][C:4]([CH:6]1[CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[N:7]1[C:15]([C:17]1[C:29](=[O:30])[N:25]2[CH2:26][CH2:27][O:28][C:23]3[C:24]2=[C:19]([CH:20]=[C:21]([O:31][CH3:32])[CH:22]=3)[C:18]=1[OH:33])=[O:16])=[O:5])C.[OH-].[Na+].C(O)C>O1CCCC1>[C:4]([CH:6]1[CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[N:7]1[C:15]([C:17]1[C:29](=[O:30])[N:25]2[CH2:26][CH2:27][O:28][C:23]3[C:24]2=[C:19]([CH:20]=[C:21]([O:31][CH3:32])[CH:22]=3)[C:18]=1[OH:33])=[O:16])([OH:5])=[O:3]

Participants

5

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 54710175HCID 54710175, compound

Product 1

HCID 54710199HCID 54710199, compoundYield 60.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 2,3-dihydro-6-(2-ethoxycarbonyl-1-indolinylcarbonyl)-7-hydroxy-9-methoxy-5-oxo-5H-pyrido[1,2,3-de]-1,4-benzoxazine (2.8 g), 1N-sodium hydroxide (20 ml), ethanol (20 ml) and tetrahydrofuran (20 ml) was stirred for 2 hours at room temperature. The solvent was evaporated. The residue was dissolved in water and washed with ethyl acetate. The aqueous layer was acidified with hydrochloric acid to give precipitates, which were collected and washed with ethanol to afford crystals of 2,3-dihydro-6-(2-carboxy-1-indolinylcarbonyl)-7-hydroxy-9-methoxy-5-oxo-5H-pyrido[1,2,3-de]-1,4-benzoxazine (1.6 g).

Workup

  1. customThe solvent was evaporated
  2. dissolutionThe residue was dissolved in water
  3. washwashed with ethyl acetate
  4. customto give
  5. customprecipitates
  6. customwhich were collected
  7. washwashed with ethanol

Sources & evidence

ORD record
ord-49a01270ca7e40c6a8adc85c8ca0364f
Source dataset
uspto-grants-1998_04
Patent number
US05739130

Reaction notes

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