Methyl chloroformate → HCID 16049828, compound

HRID 1455515Notes

Reaction equation

HRID 1455515 reaction equation
[CH3:1][O:2][C:3]1[C:4]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[N:5][C:6]2[C:11]([C:12]=1[C:13]([NH:15][NH:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:14])=[CH:10][CH:9]=[CH:8][CH:7]=2.CCN(CC)CC.Cl[C:37]([O:39][CH3:40])=[O:38]>C(Cl)Cl>[CH3:1][O:2][C:3]1[C:4]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[N:5][C:6]2[C:11]([C:12]=1[C:13]([NH:15][N:16]([C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)[C:37]([O:39][CH3:40])=[O:38])=[O:14])=[CH:10][CH:9]=[CH:8][CH:7]=2

Participants

5

Reactant 3

HCID 6586Methyl chloroformateHCID 8471TriethylamineHCID 44419758HCID 44419758, compound

Product 1

HCID 16049828HCID 16049828, compoundYield 51.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 3-methyloxy-N′,2-diphenyl-4-quinolinecarbohydrazide (100 mg, 0.27 mmol) and Et3N (56 μL, 0.41 mmol) in CH2Cl2 (7 mL) was added methyl chloroformate (27 μL, 0.35 mmol). After stirring at room temperature for 4 h the mixture was diluted with CH2Cl2 and washed with 1N HCl (20 mL), 1N NaOH (20 mL) and brine (20 mL). The organic phase was dried (MgSO4) and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel, eluting with isohexane:ethyl acetate (2:1), to afford the title compound (59 mg, 51%) as a colourless foam. 1H NMR (CDCl3, 360 MHz), δ 8.43 (1H, s), 8.16-8.13 (2H, m), 8.02-8.00 (2H, m), 7.69 (1H, dt, J=6.9 and 1.3 Hz), 7.61-7.41 (8H, m), 7.30 (1H, t, J=7.4 Hz), 3.91 (3H, s), 3.57 (3H, s). MS (ES+) C25H21N3O4 requires: 427, found: 428 (M+H+, 100%).

Workup

  1. washwashed with 1N HCl (20 mL), 1N NaOH (20 mL) and brine (20 mL)
  2. dry with materialThe organic phase was dried (MgSO4)
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by column chromatography on silica gel
  5. washeluting with isohexane:ethyl acetate (2:1)

Sources & evidence

ORD record
ord-c4bbf0fb540b4c0a8a39967e507173b7
Source dataset
uspto-grants-2009_01
Patent number
US07482457B2

Reaction notes

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