Sodium Hydroxide → HCID 118699727, compound

HRID 1773319Notes

Reaction equation

HRID 1773319 reaction equation
[S:1]1[C:13]2[C:12]3[CH2:11][CH2:10][N:9]([C:14]4[CH:15]=[C:16]([CH:21]=[CH:22][CH:23]=4)[C:17]([O:19]C)=[O:18])[CH2:8][C:7]=3[CH:6]=[N:5][C:4]=2[CH:3]=[CH:2]1.[OH-].[Na+]>O1CCOCC1>[S:1]1[C:13]2[C:12]3[CH2:11][CH2:10][N:9]([C:14]4[CH:15]=[C:16]([CH:21]=[CH:22][CH:23]=4)[C:17]([OH:19])=[O:18])[CH2:8][C:7]=3[CH:6]=[N:5][C:4]=2[CH:3]=[CH:2]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 118699712HCID 118699712, compound

Product 1

HCID 118699727HCID 118699727, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

A solution of methyl 3-(8,9-dihydrothieno[3,2-c]-2,7-naphthyridin-7(6H)-yl)benzoate (3.54 g, 10.91 mmol) in 1,4-dioxane (150 ml) was treated with 1.0 N NaOH(aq.) (32.73 ml, 32.73 mmol) and the reaction mixture was stirred at 90° C. for 3.5 hours. The solvent was removed in vacuo and the residue was partitioned between water and diethyl ether. The organic phase was discarded and the aqueous phase was acidified to pH ˜4-5 with 1.0 N HCl(aq.). The resulting precipitate was collected, washed with water, EtOAc, and dried in vacuo at 35° C. to afford the title compound as a yellow, amorphous solid (2.66 g, 79%). MS (APCl): (M+1)+=311;

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue was partitioned between water and diethyl ether
  3. customThe resulting precipitate was collected
  4. washwashed with water, EtOAc
  5. customdried in vacuo at 35° C.

Sources & evidence

ORD record
ord-916774573d304105831200ff03d1eaf4
Source dataset
uspto-grants-2016_02
Patent number
US09255096B1

Reaction notes

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