Hydrochloric Acid → HCID 21111658, compound

HRID 1766603Notes

Reaction equation

HRID 1766603 reaction equation
[Cl:1][C:2]1[CH:31]=[CH:30][CH:29]=[CH:28][C:3]=1[CH2:4][O:5][C:6]1[CH:15]=[C:14]([C:16]([O:18]CC2C=CC=CC=2Cl)=[O:17])[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([CH3:27])[CH:12]=2)[N:7]=1.[OH-].[Na+].CO.Cl>C1COCC1.O>[Cl:1][C:2]1[CH:31]=[CH:30][CH:29]=[CH:28][C:3]=1[CH2:4][O:5][C:6]1[CH:15]=[C:14]([C:16]([OH:18])=[O:17])[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([CH3:27])[CH:12]=2)[N:7]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14798Sodium HydroxideHCID 21111656HCID 21111656, compound

Product 1

HCID 21111658HCID 21111658, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

To 2-(2-chlorobenzyloxy)-4-(2-chlorobenzyloxycarbonyl)-6-methylquinoline (Method 11; 0.980 g, 2.173 mmol) in THF (100 ml) was added a solution of sodium hydroxide (261 mg, 6.519 mmol) in water (2.6 ml) followed by water (60 ml) and methanol (10 ml). The reaction mixture was stirred at ambient temperature for 2 hrs 30 min and then adjusted to pH 4–5 with 1M HCl. It was then concentrated in vacuo and the resulting solid filtered, washed with water, and dried to give the title compound as a colourless solid (0.704 g, 99%). NMR: 2.45 (3H, s), 5.60 (2H, s), 7.35 (3H, m), 7.50 (1H, m), 7.55 (1H, dd), 7.65 (1H, m), 7.75 (1H, d), 8.30 (1H, s); m/z 328 (M+H)+, 326 (M−H)−.

Workup

  1. concentrationIt was then concentrated in vacuo
  2. filtrationthe resulting solid filtered
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-047165021d274be99e147efcb7465d97
Source dataset
uspto-grants-2007_06
Patent number
US07230108B2

Reaction notes

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