Benzoyl chloride → HCID 12842041, compound

HRID 1958512Notes

Reaction equation

HRID 1958512 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH:2]1[C:10]([OH:12])=[O:11].C(N(CC)CC)C.[C:20](Cl)(=[O:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>C(Cl)Cl>[C:20]([N:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH:2]1[C:10]([OH:12])=[O:11])(=[O:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 86074Indoline-2-carboxylic acid

Product 1

HCID 12842041HCID 12842041, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of indoline-2-carboxilic acid (6.52 g, 40 mmol) and triethyl amine (11 mL, 78 mmol) in anhydrous CH2Cl2 (100 mL) was added dropwise a solution of benzoyl chloride (5.62 g, 40 mmol) in CH2Cl2 (25 mL) at 0° C. The reaction mixture was stirred at this temperature for 15 min and then at room temperature for additional 2.5 hours. The reaction mixture was washed successively with 5% aqueous KHSO4 solution (2×20 mL), brine (25 mL), dried over Na2SO4, and evaporated under reduced pressure to dryness. The residue was chromatographed on a silica gel column (3×35 cm) using CHCl3/MeOH (100:1) as the eluent. The main fractions containing the desired product was combined, evaporated under reduced pressure to dryness and the solid residue was recrystallized from MeOH to give the known 1-benzoyl-2,3-dihydro-1H-indole-2-carboxylic acid, 10.66 g (81%): mp 209-210° C. (191-193° C.)19; 1H NMR (DMSO-d6) δ 3.09 (1H, d, J=16.3 Hz, CH), 3.61-3.63 (1H, m, N—CH), 4.97 (1H, brs, CH), 7.06 (1H, m, ArH), 7.25-7.26 (2H, m, 2×ArH), 7.49 (5H, m, 5×ArH), 8.14-8.17 (1H, m, ArH), 13.01 (1H, brs, exchangeable, OH). MS: m/z 268.0 (M+H)+.

Workup

  1. waitat room temperature for additional 2.5 hours
  2. washThe reaction mixture was washed successively with 5% aqueous KHSO4 solution (2×20 mL), brine (25 mL)
  3. dry with materialdried over Na2SO4
  4. customevaporated under reduced pressure to dryness
  5. customThe residue was chromatographed on a silica gel column (3×35 cm)
  6. additionThe main fractions containing the desired product
  7. customevaporated under reduced pressure to dryness
  8. customthe solid residue was recrystallized from MeOH

Sources & evidence

ORD record
ord-452345a7e9d14bc787a63e1b251744b0
Source dataset
uspto-grants-2013_04
Patent number
US08410130B2

Reaction notes

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