Hydrochloric Acid → HCID 68161085, compound

HRID 2041721Notes

Reaction equation

HRID 2041721 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][CH3:19])(=[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][CH3:19])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 86669449HCID 86669449, compound

Product 1

HCID 68161085HCID 68161085, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
75 °C

Procedure

A suspension of (1-acetyl-6-bromo-2-ethyl-1,2,3,4-tetrahydro-4-quinolinyl)formamide (for a preparation see intermediate 4) (0.5 g, 1.538 mmol) in ethanol (4 mL) was treated with HCl (5N in water, 1 mL, 5.00 mmol) and the resulting mixture was stirred at 75° C. for 40 min under microwave irradiation then cooled to room temperature and basified with a saturated NaHCO3 aqueous solution (50 mL). 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-ethyl-1,2,3,4-tetrahydro-4-quinolinamine (377 mg, 1.27 mmol, 83%).

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-a93b697151f64e3cb40efffeb9afa22f
Source dataset
uspto-grants-2013_11
Patent number
US08580957B2

Reaction notes

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