Sodium Hydroxide → HCID 67520572, compound

HRID 1925304Notes

Reaction equation

HRID 1925304 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][C:7]([N+:15]([O-])=O)=[C:6]2[O:18][C:19]1[CH:20]=[C:21]2[C:26](=[CH:27][CH:28]=1)[C:25]([C:29]([OH:31])=[O:30])=[CH:24][CH:23]=[CH:22]2.[OH-].[Na+]>CO.[Pd]>[NH2:15][C:7]1[CH:8]=[N:9][C:10]2[C:5]([C:6]=1[O:18][C:19]1[CH:20]=[C:21]3[C:26](=[CH:27][CH:28]=1)[C:25]([C:29]([OH:31])=[O:30])=[CH:24][CH:23]=[CH:22]3)=[CH:4][C:3]([O:2][CH3:1])=[C:12]([O:13][CH3:14])[CH:11]=2

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 67519912HCID 67519912, compound

Product 1

HCID 67520572HCID 67520572, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst2×HCID 887MethanolSolvent

Procedure

Pd on carbon (5 wt %, 0.015 g) was added to a solution of 6-(6,7-dimethoxy-3-nitroquinolin-4-yloxy)-1-naphthoic acid (0.149 g, 0.354 mmol) in MeOH (30 mL). The system was purged with H2 (g) and stirred under a H2 atmosphere at RT for 21 h to afford a thick suspension. The pH of the reaction was adjusted to 6-7 with 2N NaOH (aq), and Pd on carbon (5 wt %, 0.025 g) was added to the resulting solution. The mixture was purged with H2 then stirred under a H2 atmosphere at RT for 3 days (additional Pd on carbon (5 wt %, 0.025 g) was added after the first and second days). The mixture was filtered through a pad of Celite and the filtrate was concentrated to afford 6-(3-amino-6,7-dimethoxyquinolin-4-yloxy)-1-naphthoic acid as a brown solid. MS (ESI, pos. ion) m/z: 391.1 (M+H). Mass Calc'd for C22H18N2O5: 390.

Workup

  1. customThe system was purged with H2 (g)
  2. customto afford a thick suspension
  3. additionwas added to the resulting solution
  4. customThe mixture was purged with H2
  5. stirringthen stirred under a H2 atmosphere at RT for 3 days (additional Pd on carbon (5 wt %, 0.025 g)
  6. additionwas added after the first and second days)
  7. filtrationThe mixture was filtered through a pad of Celite
  8. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-956c605efae44f198b0d2b9464318e47
Source dataset
uspto-grants-2012_05
Patent number
US08178557B2

Reaction notes

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