Methanol → 8-Carboxy-2-(dipropylamino)tetralin

HRID 1682579Notes

Reaction equation

HRID 1682579 reaction equation
Cl.[CH2:2]([N:5]([CH2:20][CH2:21][CH3:22])[CH:6]1[CH2:15][CH2:14][C:13]2[C:8](=[C:9]([C:16]([O:18]C)=[O:17])[CH:10]=[CH:11][CH:12]=2)[CH2:7]1)[CH2:3][CH3:4].[OH-].[Na+].CO>O>[C:16]([C:9]1[CH:10]=[CH:11][CH:12]=[C:13]2[C:8]=1[CH2:7][CH:6]([N:5]([CH2:20][CH2:21][CH3:22])[CH2:2][CH2:3][CH3:4])[CH2:15][CH2:14]2)([OH:18])=[O:17]

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 19044854Methyl 2-(dipropylamino)tetralin-8-carboxylate hydrochloride

Product 1

HCID 103786878-Carboxy-2-(dipropylamino)tetralinYield 97.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of methyl 2-(dipropylamino)tetralin-8-carboxylate hydrochloride (1.5 g, 4.6 mmol), sodium hydroxide (736 mg, 18.4 mmol), methanol (25 ml) and water (4 ml) was stirred overnight, The methanol was evaporated. Concentrated hydrochloric acid was added until the pH became about 6. The solution was extracted with chloroform. The organic layer was dried (sodium sulfate) and concentrated to give 1.23 g (97%) of pure 8-carboxy-2-(dipropylamino)tetralin as an oil. The hydrochloride melts at 245°-247° C., which could bse recrystallised from methanol/diethylether.

Workup

  1. customThe methanol was evaporated
  2. additionConcentrated hydrochloric acid was added until the pH
  3. extractionThe solution was extracted with chloroform
  4. dry with materialThe organic layer was dried (sodium sulfate)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-8495940f383342b5b7953186a1f6d85c
Source dataset
uspto-grants-1997_06
Patent number
US05635537

Reaction notes

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