p-Toluenesulfonic acid → 4-hydroxy-N,N,2-trimethyl-3,5-dioxo-2,3,5,6,7,8-hexahydro-2,6-naphthyridine-1-carboxamide

HRID 1817322Notes

Reaction equation

HRID 1817322 reaction equation
COC1C=CC(C[N:8]2[CH2:17][CH2:16][C:15]3[C:10](=[C:11]([O:25]C)[C:12](=[O:24])[N:13]([CH3:23])[C:14]=3[C:18]([N:20]([CH3:22])[CH3:21])=[O:19])[C:9]2=[O:27])=CC=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[OH:25][C:11]1[C:12](=[O:24])[N:13]([CH3:23])[C:14]([C:18]([N:20]([CH3:21])[CH3:22])=[O:19])=[C:15]2[C:10]=1[C:9](=[O:27])[NH:8][CH2:17][CH2:16]2

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 690582414-methoxy-6-(4-methoxybenzyl)-N,N,2-trimethyl-3,5-dioxo-2,3,5,6,7,8-hexahydro-2,6-naphthyridine-1-carboxamide

Product 1

HCID 690584564-hydroxy-N,N,2-trimethyl-3,5-dioxo-2,3,5,6,7,8-hexahydro-2,6-naphthyridine-1-carboxamide

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
110 °C

Procedure

A solution of 6-(4-methoxybenzyl)-4-methoxy-N,N, 2-trimethyl-3,5-dioxo-2,3,5,6,7,8-hexahydro-2,6-naphthyridine-1-carboxamide (0.18 g, 0.45 mmol) in toluene (about 3 mL) was treated with p-toluene sulfonic acid (0.34 g, 1.8 mmol). The mixture was heated to 110° C. for 4 hours, then cooled and concentrated under vacuum. The residue was partitioned between water and EtOAc, the aqueous layer concentrated, and the residue purified by reverse phase chromatography to give the title product.

Workup

  1. temperaturecooled
  2. concentrationconcentrated under vacuum
  3. customThe residue was partitioned between water and EtOAc
  4. concentrationthe aqueous layer concentrated
  5. customthe residue purified by reverse phase chromatography

Sources & evidence

ORD record
ord-2c6b8df332384f00882ffc7bb2aff59d
Source dataset
uspto-grants-2009_10
Patent number
US07598264B2

Reaction notes

Loading…