Hydrochloric Acid → HCID 976228, compound

HRID 1837146Notes

Reaction equation

HRID 1837146 reaction equation
N1C=CC=CC=1.[CH3:7][O:8][C:9]1[CH:10]=[C:11]([CH:13]=[CH:14][CH:15]=1)[NH2:12].[C:16]1([C:22]2[CH:30]=[CH:29][CH:28]=[CH:27][C:23]=2[C:24](Cl)=[O:25])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.Cl>ClCCl>[CH3:7][O:8][C:9]1[CH:10]=[C:11]([NH:12][C:24]([C:23]2[C:22]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[CH:30][CH:29]=[CH:28][CH:27]=2)=[O:25])[CH:13]=[CH:14][CH:15]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 108243-MethoxyanilineHCID 12563768[1,1'-Biphenyl]-2-carbonyl chloride

Product 1

HCID 976228HCID 976228, compoundYield 103.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Pyridine (3.6 mL, 45 mmol) and 3-methoxyaniline (1.54 g, 12.5 mmol) were added to a solution of 2-phenylbenzoyl chloride (3.25 g, 15 mmol) in dichloromethane (30 mL) The reaction mixture was stirred at room temperature for 2.5 hours. 1M HCl solution (45 mL) was added, and the organic layer was washed with 1M NaOH solution (10 mL), aqueous sodium bicarbonate (30 mL), and brine (30 mL). The organic phase was concentrated to dryness to give the title compound as a tan solid (3.92 g). MH+304: 1H (D6-DMSO) δ 3.67 (3H, s), 6.60 (1H, dd, J=8, 2), 7.04 (1H, d, J=8), 7.14 (1H, t, J=8), 7.18 (1H, m), 7.23-7.57 (9H, m), 10.0 (1H, s, NH).

Workup

  1. washthe organic layer was washed with 1M NaOH solution (10 mL), aqueous sodium bicarbonate (30 mL), and brine (30 mL)
  2. concentrationThe organic phase was concentrated to dryness

Sources & evidence

ORD record
ord-2b9431c5195045b49ece2ef17c1361fb
Source dataset
uspto-grants-2004_08
Patent number
US06780883B2

Reaction notes

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