Triethylamine → HCID 19699112, compound

HRID 1733969Notes

Reaction equation

HRID 1733969 reaction equation
[N:1]1[C:6]2[NH:7][CH2:8][CH2:9][CH2:10][C:11](=[O:12])[C:5]=2[CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.[Cl:20][C:21]1[CH:29]=[C:28]([N+:30]([O-:32])=[O:31])[CH:27]=[CH:26][C:22]=1[C:23](Cl)=[O:24]>ClCCl>[Cl:20][C:21]1[CH:29]=[C:28]([N+:30]([O-:32])=[O:31])[CH:27]=[CH:26][C:22]=1[C:23]([N:7]1[CH2:8][CH2:9][CH2:10][C:11](=[O:12])[C:5]2[CH:4]=[CH:3][CH:2]=[N:1][C:6]1=2)=[O:24]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 81522Benzoyl chloride, 2-chloro-4-nitro-HCID 196991086,7,8,9-Tetrahydro-5H-pyrido[2,3-b]azepin-5-one

Product 1

HCID 19699112HCID 19699112, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 6,7,8,9-tetrahydro-5H-pyrido[2,3-b]azepin-5-one and 0.234 g of triethylamine in 6 ml of dichloromethane is added 0.506 g of 2-chloro-4-nitrobenzoyl chloride in 2 ml of dichloromethane. The mixture is stirred at room temperature overnight under argon. The solution is washed with H2O, 10% NaHCO3 and dried (MgSO4). The solvent is removed to give a brown oil which crystallizes. The mixture is chromatographed on silica with a waters Prep-500 instrument with ethyl acetate-hexane (1:1) as solvent to give 2.4 g of off-white crystals, m.p. 162°-164° C. (identified as O-2-chloro-4-nitrobenzoyl derivative (2-chloro-4-nitrobenzoyl enolate of product) and 0.80 g of product as crystals, m.p. slowly decomposes 160°-220° C.

Workup

  1. washThe solution is washed with H2O, 10% NaHCO3
  2. dry with materialdried (MgSO4)
  3. customThe solvent is removed
  4. customto give a brown oil which
  5. customcrystallizes
  6. customThe mixture is chromatographed on silica with a waters

Sources & evidence

ORD record
ord-fa290a9264d540b9b378e6d8eee2a3b3
Source dataset
uspto-grants-1996_07
Patent number
US05532235

Reaction notes

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