Hydrochloric Acid → HCID 67206982, compound

HRID 2041718Notes

Reaction equation

HRID 2041718 reaction equation
[C:1]([N:4]1[C:13]2[C:8](=[CH:9][C:10]([Br:14])=[CH:11][CH:12]=2)[CH:7]([NH:15]C=O)[CH2:6][CH:5]1[CH2:18][CH2:19][CH3:20])(=[O:3])[CH3:2].Cl.C([O-])(O)=O.[Na+]>C(O)C>[C:1]([N:4]1[C:13]2[C:8](=[CH:9][C:10]([Br:14])=[CH:11][CH:12]=2)[C@H:7]([NH2:15])[CH2:6][C@@H:5]1[CH2:18][CH2:19][CH3:20])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 86669446HCID 86669446, compound

Product 1

HCID 67206982HCID 67206982, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
75 °C

Procedure

(1-acetyl-6-bromo-2-propyl-1,2,3,4-tetrahydro-4-quinolinyl)formamide (for a preparation see intermediate 88) (0.5 g, 1.474 mmol) was suspended in ethanol (4 mL) and treated with HCl (5N in water, 1 ml, 5.00 mmol). The resulting mixture was stirred at 75° C. for 40 min under microwave irradiation then cooled to room temperature. The reaction mixture was basified with a saturated NaHCO3 aqueous solution (50 mL), and the aqueous phase was extracted with AcOEt (3×50 mL). The combined organic phases were dried over MgSO4 then concentrated in vacuo to give (cis)-1-acetyl-6-bromo-2-propyl-1,2,3,4-tetrahydro-4-quinolinamine (399 mg, 1.28 mmol, 87%)

Workup

  1. temperaturethen cooled to room temperature
  2. extractionthe aqueous phase was extracted with AcOEt (3×50 mL)
  3. dry with materialThe combined organic phases were dried over MgSO4
  4. concentrationthen concentrated in vacuo

Sources & evidence

ORD record
ord-0c2ad309cb0c454a82e7af3f133165a8
Source dataset
uspto-grants-2013_11
Patent number
US08580957B2

Reaction notes

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