2-Methoxyaniline → 36684-47-6

HRID 2355235Notes

Reaction equation

HRID 2355235 reaction equation
[CH3:1][O:2][C:3]1[CH:9]=[CH:8][CH:7]=[CH:6][C:4]=1[NH2:5].CCN(CC)CC.[I:17][C:18]1[CH:26]=[CH:25][CH:24]=[CH:23][C:19]=1[C:20](Cl)=[O:21]>C(Cl)Cl>[I:17][C:18]1[CH:26]=[CH:25][CH:24]=[CH:23][C:19]=1[C:20]([NH:5][C:4]1[CH:6]=[CH:7][CH:8]=[CH:9][C:3]=1[O:2][CH3:1])=[O:21]

Participants

5

Reactant 3

HCID 70002-MethoxyanilineHCID 8471TriethylamineHCID 691122-Iodobenzoyl chloride

Product 1

HCID 61589336684-47-6Yield 80.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To a solution of 2-methoxyaniline 5 (2.46 g, 20 mmol) in dry CH2Cl2 (50 mL) was added Et3N (6.14 mL, 44 mmols) at 0° C. and under dry N2 atmosphere. A solution 2-iodobenzoyl chloride 2 (5.33 g, 20 mmol) in dry CH2Cl2 (25 mL) was slowly added to the reaction mixture keeping the temperature at 0° C. After 15 min the reaction mixture was allowed to warm to room temperature and stirred overnight. Reaction mixture was diluted with CH2Cl2 (100 mL), washed with H2O (40 mL) and saturated aqueous NaCl solution (40 mL), dried (Na2SO4) and evaporated to yield a light pink solid. Recrystallization from ethyl acetate-hexanes (1:3) provided 3 as white needles (5.7 g). The filtrate was concentrated and the residue was purified by flash chromatography on silica, eluting with 15% ethyl acetate (EtOAc) in hexanes, to provide additional pure product (1.25 g). Total yield: 6.95 g, 98%; 1H NMR (400 MHz, CDCl3) δ 8.54 (dd, J=8.0, 2.0 Hz, 1H), 8.10 (br s, 1H), 7.92 (dd, J=8.0, 1.2 Hz, 1H), 7.52 (dd, J=7.6, 1.2 Hz, 1H), 7.43 (ddd, J=8.8, 7.6, 1.2 Hz, 1H), 7.17-7.09 (m, 2H), 7.03 (t, J=8.0 Hz, 1H), 6.92 (d, J=8.0 Hz, 1H), 3.87 (s, 3H); 13C NMR (100 MHz, CDCl3) δ 167.10, 148.29, 142.58, 140.30, 131.49, 128.52, 128.43, 127.58, 124.45, 121.33, 120.12, 110.25, 92.70, 55.92; MS (ESI): m/z 376.20 (M+Na)+.

Workup

  1. customat 0° C
  2. customReaction mixture
  3. washwashed with H2O (40 mL) and saturated aqueous NaCl solution (40 mL)
  4. dry with materialdried (Na2SO4)
  5. customevaporated
  6. customto yield a light pink solid
  7. customRecrystallization from ethyl acetate-hexanes (1:3)

Sources & evidence

ORD record
ord-33308e3507dc41f9afdbc94518b76f5f
Source dataset
uspto-grants-2010_07
Patent number
US07754773B2

Reaction notes

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