Sulfuric acid magnesium salt (1:1) → HCID 67994951, compound

HRID 2361373Notes

Reaction equation

HRID 2361373 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[CH:14]=[C:13]2[C:9]([CH:10]=[C:11]([C:15]([O:17][CH3:18])=[O:16])[NH:12]2)=[CH:8][CH:7]=1.Cl[Sn](Cl)(Cl)Cl.C(Cl)Cl.[CH3:27][C:28]1[C:36]([N+:37]([O-:39])=[O:38])=[CH:35][CH:34]=[CH:33][C:29]=1[C:30](Cl)=[O:31].[O-]S([O-])(=O)=O.[Mg+2]>ClCCl.[N+](C)([O-])=O.CCOC(C)=O>[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[CH:14]=[C:13]2[C:9]([C:10]([C:30](=[O:31])[C:29]3[CH:33]=[CH:34][CH:35]=[C:36]([N+:37]([O-:39])=[O:38])[C:28]=3[CH3:27])=[C:11]([C:15]([O:17][CH3:18])=[O:16])[NH:12]2)=[CH:8][CH:7]=1

Participants

8

Reactant 4

HCID 24083Sulfuric acid magnesium salt (1:1)HCID 121948722-Methyl-3-nitrobenzoyl chlorideHCID 68827000HCID 68827000, compoundHCID 86681524HCID 86681524, compound

Product 1

HCID 67994951HCID 67994951, compoundYield 104%

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolventHCID 6375NitromethaneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a homogeneous, colorless solution of methyl 6-(2-methoxyethoxy)-1H-indole-2-carboxylate (0.934 g, 3.75 mmol) in dichloromethane (18.74 mL) at 0° C. under nitrogen was added 1M perchlorostannane/CH2Cl2 (4.87 mL, 4.87 mmol) over 10 min. After 5 min, the cold bath was removed, and the yellow, heterogeneous solution was stirred to room temperature for 30 min. A solution of 2-methyl-3-nitrobenzoyl chloride (0.897 g, 4.50 mmol) in nitromethane (18.74 mL, previously dried over MgSO4 overnight) was added over 20 min. After 3.25 hr, additional acid chloride (0.350 g) in nitromethane (3 mL) was added to the reaction. Thirty minutes later, the reaction was poured into ice water (50 mL) and stirred for 15 min. It was diluted with EtOAc (150 mL) and washed with water (50 mL), sat. aq. NaHCO3 (50 mL) and brine (25 mL). The organic solution was dried over MgSO4 and concentrated in vacuo to give the desired product (1.6103 g, 3.90 mmol, 104% yield) as a solid.

Workup

  1. customthe cold bath was removed
  2. additionwas added over 20 min
  3. waitAfter 3.25 hr
  4. stirringstirred for 15 min
  5. washwashed with water (50 mL), sat. aq. NaHCO3 (50 mL) and brine (25 mL)
  6. dry with materialThe organic solution was dried over MgSO4
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b8050de753704a2693813230759f4c9c
Source dataset
uspto-grants-2014_04
Patent number
US08685969B2

Reaction notes

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