Hydrochloric Acid → HCID 86669233, compound

HRID 2366850Notes

Reaction equation

HRID 2366850 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].[Br:5][C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[NH:12][C@@H:11]([CH3:16])[CH2:10][C@H:9]2[NH:17][CH:18]=[O:19].Cl>C(Cl)Cl.N1C=CC=CC=1>[C:1]([N:12]1[C:13]2[C:8](=[CH:7][C:6]([Br:5])=[CH:15][CH:14]=2)[C@H:9]([NH:17][CH:18]=[O:19])[CH2:10][C@@H:11]1[CH3:16])(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 6367Acetyl chlorideHCID 86669234HCID 86669234, compound

Product 1

HCID 86669233HCID 86669233, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Acetyl chloride (21 mL, 0.29 mol) was added dropwise at 0° C. to a solution of ((cis)-6-bromo-2-methyl-1,2,3,4-tetrahydro-4-quinolinyl)formamide (for a preparation see Intermediate 41) (71 g, 0.26 mol) in a mixture of DCM (1 L) and pyridine (350 mL). After stirring 2 hours at 0° C. the mixture was poured into a mixture of crushed ice (2 kg) and concentrated HCl (450 mL). The product was extracted with DCM (1 L) washed with brine and dried over Na2SO4. Concentration under vacuo afforded the expected product as an off white solid (82 g, 100%).

Workup

  1. extractionThe product was extracted with DCM (1 L)
  2. washwashed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationConcentration under vacuo

Sources & evidence

ORD record
ord-449a4d3594e04a42876ca485a3c757a3
Source dataset
uspto-grants-2014_04
Patent number
US08697725B2

Reaction notes

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