Hydrochloric Acid → HCID 57742965, compound

HRID 1801977Notes

Reaction equation

HRID 1801977 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[N:7][CH:8]=[C:9]([I:12])[CH:10]=2)[N:5]([CH3:13])[C:4](=[O:14])[CH:3]=1.Cl.O[C:17]1[C:26]2C(=NC=C(I)C=2)N(C)C(=O)[C:18]=1[C:30]([O:32]C)=[O:31].C(O)(C(F)(F)F)=[O:35]>>[OH:1][C:2]1[C:11]2[C:6](=[N:7][CH:8]=[C:9]([I:12])[CH:10]=2)[N:5]([CH3:13])[C:4](=[O:14])[C:3]=1[C:26](=[O:35])[CH2:17][CH2:18][C:30]([OH:32])=[O:31]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 6422Trifluoroacetic acidHCID 57671585HCID 57671585, compoundHCID 67408381HCID 67408381, compound

Product 1

HCID 57742965HCID 57742965, compoundYield 96%

Conditions

Temperature
80 °C

Procedure

4-Hydroxy-6-iodo-1-methyl-1,8-naphthyridin-2(1H)-one. Concentrated aqueous HCl (10 mL) was added to a solution of methyl 4-hydroxy-6-iodo-1-methyl-2-oxo-1,2-dihydro-1,8-naphthyridine-3-carboxylate (Method 2) (1.00 g, 2.78 mmol) in TFA (10 mL). The mixture was heated at 80° C. for 18 hours. The solvent was removed, and the residue rinsed with water and diethyl ether. The product was dried in a vacuum oven at 50° C. to afford the title compound in 96% yield. 1H-NMR (300 MHz, DMSO-d6) δ ppm 11.84 (1 H, s), 8.82 (1H, d, J=2.3 Hz), 8.43 (1H, d, J=2.3 Hz), 5.89 (1H, s), 3.39 (3 H, s). MS m/z: 303 (M+).

Workup

  1. customThe solvent was removed
  2. washthe residue rinsed with water and diethyl ether
  3. customThe product was dried in a vacuum oven at 50° C.

Sources & evidence

ORD record
ord-db6616907a944011a56a667b15c0a9e7
Source dataset
uspto-grants-2013_01
Patent number
US08349868B2

Reaction notes

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