Hydrochloric Acid → 6-Iodo-7-methoxy-1-methyl-4-oxo-1,4-dihydro[1,8]naphthyridine-3-carboxylic acid

HRID 1280462Notes

Reaction equation

HRID 1280462 reaction equation
[I:1][C:2]1[CH:3]=[C:4]2[C:9](=[N:10][C:11]=1[O:12][CH3:13])[N:8]([CH3:14])[CH:7]=[C:6]([C:15]([O:17]CC)=[O:16])[C:5]2=[O:20].[OH-].[Na+].Cl>CO>[I:1][C:2]1[CH:3]=[C:4]2[C:9](=[N:10][C:11]=1[O:12][CH3:13])[N:8]([CH3:14])[CH:7]=[C:6]([C:15]([OH:17])=[O:16])[C:5]2=[O:20]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 12093314Ethyl 6-iodo-7-methoxy-1-methyl-4-oxo-1,4-dihydro[1,8]naphthyridine-3-carboxylate

Product 1

HCID 120933156-Iodo-7-methoxy-1-methyl-4-oxo-1,4-dihydro[1,8]naphthyridine-3-carboxylic acidYield 96%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Ethyl 6-iodo-7-methoxy-1-methyl-4-oxo-1,4-dihydro[1,8]naphthyridine-3-carboxylate (3.63 g) is dissolved in MeOH (200 mL). To this is added 6N NaOH (60 mL) and the resulting mixture is stirred at room temperature for 4 h. The white suspension is poured into a seperatory funnel and the organic layer is made acidic with HCl, extracted several times with CH2Cl2 (total volume 4 L), washed with water, brine, dried (MgSO4), filtered and concentrated in vacuo to afford 3.2 g (96%) of 6-iodo-7-methoxy-1-methyl-4-oxo-1,4-dihydro[1,8]naphthyridine-3-carboxylic acid. Physical characteristics are as follows: 1H NMR (CDCl3) δ 14.62, 9.09, 8.81, 4.19, 4.05; IR (diffuse reflectance) 2497, 2350, 2338, 2086, 1990, 1720, 1716, 1628, 1525, 1482, 1464, 1448, 1385, 1278, 810, cm−1; MS (EI) m/z 360, 316, 185, 159, 158, 142, 86, 84, 63, 53, 51; Anal calcd for C11H9IN2O4: C, 36.69; H, 2.52; N, 7.78. Found: C, 36.93; H, 2.57; N, 7.77.

Workup

  1. additionThe white suspension is poured into a seperatory funnel
  2. extractionextracted several times with CH2Cl2 (total volume 4 L)
  3. washwashed with water, brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9fe0fcaaa8234ede85854a7e87814ebb
Source dataset
uspto-grants-2002_09
Patent number
US06451811B2

Reaction notes

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