Methyl anisate → NSC685853

HRID 1071218Notes

Reaction equation

HRID 1071218 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9]C)=O)=[CH:5][CH:4]=1.[CH3:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([CH2:21][C:22]#[N:23])=[CH:17][CH:16]=1.[Li+].CC([N-]C(C)C)C>C1COCC1>[NH2:23][C:22]1[C:5]2[C:6](=[CH:11][CH:12]=[C:3]([O:2][CH3:1])[CH:4]=2)[C:7](=[O:9])[C:21]=1[C:18]1[CH:19]=[CH:20][C:15]([O:14][CH3:13])=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 8499Methyl anisateHCID 66031Benzeneacetonitrile, 4-methoxy-HCID 2724682Lithium diisopropylamide

Product 1

HCID 389548NSC685853Yield 65%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of methyl 4-methoxybenzoate (1.47 g, 7.47 mmole) and 4-methoxy phenylacetonitrile (1.00 g, 6.79 mmole) in dry THF (15 mL) was slowly added to 20 ml of 2.0 M of LDA at −10° C. The mixture was gradually allowed to warm to room temperature and left to stir overnight. The reaction was quenched with water and most of the THF was removed via vacuum. The crude aminoindenone was then filtered, dried and recrystallized from isopropanol to give a red orange solid (65% yield, m.p. 213° C.); MS m/e 281 (M+)+.

Workup

  1. waitleft
  2. customThe reaction was quenched with water and most of the THF
  3. customwas removed via vacuum
  4. filtrationThe crude aminoindenone was then filtered
  5. customdried
  6. customrecrystallized from isopropanol

Sources & evidence

ORD record
ord-e6ddc0bdb53d402496282507f7e259f0
Source dataset
uspto-grants-2005_06
Patent number
US06903238B2

Reaction notes

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