Ethanol → HCID 54710199, compound

HRID 1080646Notes

Reaction equation

HRID 1080646 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.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

4

Reactant 2

HCID 702EthanolHCID 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-5Hpyrido[1,2,3-de]-1,4-benzoxazine (2.8 g), 1N-sodium 35 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-36039cd7001f4237ad66ef32cf0c8db7
Source dataset
uspto-grants-1996_12
Patent number
US05583135

Reaction notes

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