Acetyl chloride → HCID 18765146, compound

HRID 1059714Notes

Reaction equation

HRID 1059714 reaction equation
[CH3:1][C:2]1[CH:11]=[CH:10][C:9]2[CH2:8][NH:7][CH2:6][CH2:5][C:4]=2[N:3]=1.C(N(CC)CC)C.[C:19](Cl)(=[O:21])[CH3:20]>C(Cl)Cl>[C:19]([N:7]1[CH2:6][CH2:5][C:4]2[N:3]=[C:2]([CH3:1])[CH:11]=[CH:10][C:9]=2[CH2:8]1)(=[O:21])[CH3:20]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 13193883HCID 13193883, compound

Product 1

HCID 18765146HCID 18765146, compoundYield 93.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-methyl-5,6,7,8-tetrahydro-1,6-naphthyridine [Shiozawa et al., Chem. Pharm. Bull., 32 2522, (1984)] (2.73 g, 0.0184 mol) in CH2Cl2 (30 ml) and triethylamine (5.1 ml, 0.0368 mol) was added acetyl chloride (1.57 ml, 0.0221 mol) at 0° C. The reaction mixture was stirred for 24 h at room temperature, after which time the reaction mixture was washed sequentially with saturated aqueous sodium bicarbonate, H2O, saturated brine, dried over MgSO4 and evaporated under reduced pressure to afford the subtitle compound (3.27 g, 93%). Rf 0.5 (CH2Cl2/MeOH/0.88NH3 90/10/1, v/v). MS m/z 191 (MH+).

Workup

  1. washafter which time the reaction mixture was washed sequentially with saturated aqueous sodium bicarbonate, H2O, saturated brine
  2. dry with materialdried over MgSO4
  3. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-ea113e56afce435483a93bcde19086e2
Source dataset
uspto-grants-2003_02
Patent number
US06521629B2

Reaction notes

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