4-Chloroaniline → HCID 44542118, compound

HRID 1483216Notes

Reaction equation

HRID 1483216 reaction equation
CO[C:3]1[C:4](=[O:10])[C:5](=[O:9])[C:6]=1[O:7][CH3:8].[Cl:11][C:12]1[CH:18]=[CH:17][C:15]([NH2:16])=[CH:14][CH:13]=1>CO>[Cl:11][C:12]1[CH:18]=[CH:17][C:15]([NH:16][C:3]2[C:4](=[O:10])[C:5](=[O:9])[C:6]=2[O:7][CH3:8])=[CH:14][CH:13]=1

Participants

4

Reactant 2

HCID 78124-ChloroanilineHCID 1232273-Cyclobutene-1,2-dione, 3,4-dimethoxy-

Product 1

HCID 44542118HCID 44542118, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a stirred mixture of 3,4-dimethoxycyclobut-3-ene-1,2-dione (O1, 1.00 g, 7.04 mmol) in methanol (7 mL) at 0° C. under nitrogen was added a solution of 4-chloroaniline (0.898 g, 7.04 mmol) in methanol (8 mL) dropwise over 0.5 h. After addition, the reaction mixture was slowly warmed to room temperature and stirred at room temperature for another 2 days. The reaction mixture was filtered. The filter cake was washed with cold methanol (5 mL) and dried under reduced pressure to afford compound O2 as a yellow solid (1.48 g, 89%): 1H NMR (300 MHz, DMSO-d6) δ 10.84 (s, 1H), 7.44-7.35 (m, 4H), 4.38 (s, 3H). MS (M+H) 238.

Workup

  1. additionAfter addition
  2. filtrationThe reaction mixture was filtered
  3. washThe filter cake was washed with cold methanol (5 mL)
  4. customdried under reduced pressure

Sources & evidence

ORD record
ord-ca91d47e27054239b07521859890e8c6
Source dataset
uspto-grants-2016_08
Patent number
US09416141B2

Reaction notes

Loading…