Water → Ethyl 4-hydroxy-6-iodo-1-methyl-2-oxo-1,2-dihydroquinoline-3-carboxylate

HRID 1801987Notes

Reaction equation

HRID 1801987 reaction equation
[I:1][C:2]1[CH:14]=[CH:13][C:5]2[N:6]([CH3:12])[C:7](=[O:11])O[C:9](=[O:10])[C:4]=2[CH:3]=1.I[C:16]1C=CC(NC)=C([CH:24]=1)C(O)=O.[C:27](=[O:30])([O-])[O-:28].[Na+].[Na+].O.[C:34](Cl)(Cl)=O>C1(C)C=CC=CC=1>[OH:10][C:9]1[C:4]2[C:5](=[CH:13][CH:14]=[C:2]([I:1])[CH:3]=2)[N:6]([CH3:12])[C:7](=[O:11])[C:34]=1[C:27]([O:28][CH2:16][CH3:24])=[O:30]

Participants

7

Reactant 5

HCID 962WaterHCID 6371PhosgeneHCID 10340Sodium CarbonateHCID 222818675-Iodo-2-(methylamino)benzoic acidHCID 538260965-iodo-N-methylisatoic anhydride

Product 1

HCID 59340095Ethyl 4-hydroxy-6-iodo-1-methyl-2-oxo-1,2-dihydroquinoline-3-carboxylate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

6-Iodo-1-methyl-1H-benzo[d][1,3]oxazine-2,4-dione. To a stirred solution of 5-iodo-2-(methylamino)benzoic acid (10 g, 36 mmol), sodium carbonate (4 g, 36 mmol) and water (130 mL, 7218 mmol), cooled to 0° C., was slowly added, via addition funnel, a 2M phosgene (18 mL, 36 mmol) solution in toluene. After 2 hours, the precipitated product was isolated by filtration. The solids were washed with 100 mL of water, 150 mL of a 1:1 mixture of EtOH and ether, 100 mL of ether, and dried under vacuum to give the title compound.

Workup

  1. additionwas slowly added, via addition funnel
  2. customthe precipitated product was isolated by filtration
  3. washThe solids were washed with 100 mL of water, 150 mL of a 1:1 mixture of EtOH and ether, 100 mL of ether
  4. customdried under vacuum

Sources & evidence

ORD record
ord-edf8a3af708544a2a9898caaa3d00912
Source dataset
uspto-grants-2013_01
Patent number
US08349868B2

Reaction notes

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