Sodium Hydroxide → HCID 68699381, compound

HRID 2235157Notes

Reaction equation

HRID 2235157 reaction equation
C[O:2][C:3]([C:5]1[CH:14]=[C:13]2[C:8]([CH2:9][CH2:10][CH2:11][N:12]2[C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])=[CH:7][CH:6]=1)=[O:4].[OH-].[Na+]>CO>[C:18]([O:17][C:15]([N:12]1[C:13]2[C:8](=[CH:7][CH:6]=[C:5]([C:3]([OH:4])=[O:2])[CH:14]=2)[CH2:9][CH2:10][CH2:11]1)=[O:16])([CH3:21])([CH3:19])[CH3:20]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 68693747HCID 68693747, compound

Product 1

HCID 68699381HCID 68699381, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of crude 3,4-dihydro-2H-quinoline-1,7-dicarboxylic acid 1-tert-butyl ester 7-methyl ester (2.7 g, 9.2 mmol) in methanol (30 ml) was treated with 3N NaOH (10 ml, 30 mmol, 3.3 equiv.) and stirred at room temperature for 5 h. The methanol was evaporated and the residual slurry was treated with 3N HCl (10 ml). The white precipitate was filtered, washing with water, and dried under high vacuum to afford 3,4-dihydro-2H-quinoline-1,7-dicarboxylic acid 1-tert-butyl ester as a white solid, 2.5 g (97%). MS (ISP): m/e=276.1 (M−H); δH (300 MHz; CDCl3) 8.40 (0.25H, s), 8.33 (0.75H, s), 7.70 (0.25H, d), 7.64 (0.75H, d), 7.14 (1H, m), 3.75 (2H, m), 2.82 (2H, m), 1.94 (2H, m), 1.54 (9H, s).

Workup

  1. customThe methanol was evaporated
  2. additionthe residual slurry was treated with 3N HCl (10 ml)
  3. filtrationThe white precipitate was filtered
  4. washwashing with water
  5. customdried under high vacuum

Sources & evidence

ORD record
ord-4ef65c5c0a144696bb285d8e9a3059f7
Source dataset
uspto-grants-2010_05
Patent number
US07713996B2

Reaction notes

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