Sodium Hydroxide → HCID 69018669, compound

HRID 1865203Notes

Reaction equation

HRID 1865203 reaction equation
C([O:3][C:4]([C:6]1[NH:7][C:8]2[C:13]([CH:14]=1)=[CH:12][C:11]([O:15][C:16]1[C:25]3[C:20](=[CH:21][C:22]([O:28][CH3:29])=[C:23]([O:26][CH3:27])[CH:24]=3)[N:19]=[CH:18][CH:17]=1)=[CH:10][CH:9]=2)=[O:5])C.[OH-].[Na+]>C1COCC1.CO>[CH3:27][O:26][C:23]1[CH:24]=[C:25]2[C:20](=[CH:21][C:22]=1[O:28][CH3:29])[N:19]=[CH:18][CH:17]=[C:16]2[O:15][C:11]1[CH:12]=[C:13]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([C:4]([OH:5])=[O:3])=[CH:14]2

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 57756359HCID 57756359, compound

Product 1

HCID 69018669HCID 69018669, compound

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To a solution of 5-(6,7-dimethoxy-quinolin-4-yloxy)-1H-indole-2-carboxylic acid ethyl ester (0.2 g, 0.51 mmol, from step a) in 1:1 THF/MeOH (4 mL) was added 1.53 mL of 1N NaOH. The reaction was stirred at RT for 16 h then concentrated in vacuo. The remaining solution was acidified with 10% HCl to pH ˜5. The white precipitate was collected, dried in vacuo to afford white solid as desired acid. MS (ESI pos. ion) m/z: 365 (M+H). Calc'd Exact Mass for C20H16N2O5: 364.35.

Workup

  1. concentrationthen concentrated in vacuo
  2. customThe white precipitate was collected
  3. customdried in vacuo
  4. customto afford white solid as desired acid

Sources & evidence

ORD record
ord-f1d99584cb0e46b08ad1c12e4593c493
Source dataset
uspto-grants-2009_12
Patent number
US07626030B2

Reaction notes

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