Triethylamine → 4-chloro-N-{3-methoxy-4-[2-(1-pyrrolidinyl)ethoxy]phenyl}-2-nitrobenzamide

HRID 1181361Notes

Reaction equation

HRID 1181361 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:7]=[CH:8][C:9]=1[O:10][CH2:11][CH2:12][N:13]1[CH2:17][CH2:16][CH2:15][CH2:14]1)[NH2:6].C(N(CC)CC)C.[Cl:25][C:26]1[CH:34]=[CH:33][C:29]([C:30](Cl)=[O:31])=[C:28]([N+:35]([O-:37])=[O:36])[CH:27]=1>C(Cl)Cl>[Cl:25][C:26]1[CH:34]=[CH:33][C:29]([C:30]([NH:6][C:5]2[CH:7]=[CH:8][C:9]([O:10][CH2:11][CH2:12][N:13]3[CH2:17][CH2:16][CH2:15][CH2:14]3)=[C:3]([O:2][CH3:1])[CH:4]=2)=[O:31])=[C:28]([N+:35]([O-:37])=[O:36])[CH:27]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 108677844-Chloro-2-nitrobenzoyl chlorideHCID 117365033-Methoxy-4-(2-(pyrrolidin-1-yl)ethoxy)aniline

Product 1

HCID 589808694-chloro-N-{3-methoxy-4-[2-(1-pyrrolidinyl)ethoxy]phenyl}-2-nitrobenzamideYield 69%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-methoxy-4-[2-(1-pyrrolidinyl)ethoxy]aniline (43 mmol, 10.0 g) in DCM was added triethylamine (52 mmol, 5.2 g) and 4-chloro-2-nitrobenzoyl chloride (9.5 g, 43 mmol). The solution was stirred overnight. The reaction mixture was extracted with 2N HCl. The resulting acidic aqueous solution was made basic by adding 2N NaOH. The combined basic aqueous solution was extracted with DCM. The organic phase was washed with brine, dried and concentrated giving the title compound (11.5 g, 69%). 1H NMR (DMSO-D6): δ 1.66 (4H, m), 2.49 (4H, m), 2.75 (2H, t, J=6.0 Hz), 3.72 (3H, s), 4.00 (2H, t, J=6.0 Hz), 6.94 (1H, d, J=8.6 Hz), 7.14 (1H, d, J=8.6 Hz), 7.79 (1H, d, J=8.1 Hz), 7.94 (1H, d, J=8.1 Hz), 8.23 (1H, s), 10.55 (1H, s). LCMS m/z=420 (m+H+).

Workup

  1. extractionThe reaction mixture was extracted with 2N HCl
  2. additionby adding 2N NaOH
  3. extractionThe combined basic aqueous solution was extracted with DCM
  4. washThe organic phase was washed with brine
  5. customdried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-a822c74cca6540a7be14b399ff1e7a18
Source dataset
uspto-grants-2007_10
Patent number
US07285557B2

Reaction notes

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