N-Methyl-m-anisidine → HCID 14742779, compound

HRID 1651273Notes

Reaction equation

HRID 1651273 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][CH:10]=1)[NH:6][CH3:7].Cl[CH:12]([C:15](=[O:21])[CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])[C:13]#[N:14]>C(O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][CH:10]=1)[N:6]([CH:12]([C:15](=[O:21])[CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])[C:13]#[N:14])[CH3:7]

Participants

4

Reactant 2

HCID 84349N-Methyl-m-anisidineHCID 14742778HCID 14742778, compound

Product 1

HCID 14742779HCID 14742779, compoundYield 65.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 3-methoxy-N-methylaniline (9.8 g) and 2-chloro-3-oxooctanenitrile (6.2 g) in ethanol (25 mL) was heated at reflux for 17 hours then the solvent was removed under reduced pressure. The residue was dissolved in dichloromethane (100 mL) and washed with 1N hydrochloric acid (3×50 mL). The aqueous layers were backwashed in turn with dichloromethane (50 mL) and the combined organic layers were dried (K2CO3) and evaporated. The residual oil was purified by HPLC (diethyl ether-hexane; 3:7) to yield 6.42 g of 2-(3-methoxy-N-methylanilino)-3-oxooctanenitrile as an oil. The above material was dissolved in trifluoroacetic acid (15 mL) and the solution was allowed to stand overnight at ambient temperature. The solvent was then evaporated and the residue was partitioned between dichloromethane (100 mL) and 1N sodium hydroxide solution (100 mL). The dried (K2CO3) organic layer was evaporated and the residue was purified by HPLC (diethyl ether-hexane; 1:1) to give 3.2 g of 6-methoxy-1-methyl-3-pentyl-2-indolecarbonitrile as an oil.

Workup

  1. temperatureat reflux for 17 hours
  2. customthe solvent was removed under reduced pressure
  3. dissolutionThe residue was dissolved in dichloromethane (100 mL)
  4. washwashed with 1N hydrochloric acid (3×50 mL)
  5. dry with materialthe combined organic layers were dried (K2CO3)
  6. customevaporated
  7. customThe residual oil was purified by HPLC (diethyl ether-hexane; 3:7)

Sources & evidence

ORD record
ord-74d46badb40741da9d6bcf51615518d6
Source dataset
uspto-grants-1990_05
Patent number
US04927838

Reaction notes

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