Triethylamine → HCID 21184807, compound

HRID 1419419Notes

Reaction equation

HRID 1419419 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH3:10])=[C:6](Br)[C:5]=1[OH:12])([O-:3])=[O:2].[CH2:13]([N:15](CC)CC)C.CN(C1C=CC=CN=1)C.[Cu]C#N>CN(C)C=O>[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH3:10])=[C:6]([C:13]#[N:15])[C:5]=1[OH:12])([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 218852-DimethylaminopyridineHCID 21714401182499-91-8HCID 178418546HCID 178418546, compound

Product 1

HCID 21184807HCID 21184807, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

2-Nitro-5-methyl-6-bromophenol (100 mg, 0.433 mmol) was dissolved in dimethyl formamide (2 mL) followed by the addition of triethylamine (0.175 g, 1.73 mmol). The addition of a catalytic amount dimethylamino pyridine was then made, followed by addition of copper (I) cyanide (155 mg, 1.73 mmol). The mixture was allowed to stir at 80° C. for 4 hours. The solvent was evaporated and chromatography of the resulting solid on silica gel (2% MeOH/CH2Cl2) gave the desired product (70 mg, 91%). 1H NMR (CD3COCD3): δ 8.30 (d, 1H), 7.15 (d, 1H), 2.61 (s, 3H).

Workup

  1. customThe solvent was evaporated

Sources & evidence

ORD record
ord-569acf35ad4144f7b19f4ba3f31c714f
Source dataset
uspto-grants-1999_03
Patent number
US05886044

Reaction notes

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