Trimethylsilyldiazomethane → HCID 68862597, compound

HRID 1725909Notes

Reaction equation

HRID 1725909 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]=1[C:12]([OH:14])=[O:13].[CH3:15][Si](C=[N+]=[N-])(C)C>C1C=CC=CC=1.CO>[CH3:15][C:11]1[C:2]([NH2:1])=[C:3]([C:12]([OH:14])=[O:13])[C:4]2[C:9]([CH:10]=1)=[CH:8][CH:7]=[CH:6][CH:5]=2

Participants

4

Reactant 2

HCID 167693TrimethylsilyldiazomethaneHCID 127450062-Aminonaphthalene-1-carboxylic acid

Product 1

HCID 68862597HCID 68862597, compoundYield 93.9%

Reagents, catalysts & solvents 1

HCID 21927730Benzene methanolSolvent

Procedure

2-Amino-1-naphthoic acid (3.21 g, 17.2 mmol) in 4:1 benzene/CH3OH (125 mL) was treated with trimethylsilyldiazomethane (9.0 mL, 18.0 mmol, 2.0M solution in hexanes), stirred for 2.5 hours, quenched with acetic acid (0.5 mL), and concentrated. The concentrate was purified by flash column chromatography (4:1 hexanes/ethyl acetate) to provide the desired compound (3.25 g). MS (ESI(+)) m/e 202 (M+H)+; (ESI(−)) m/e 200 (M−H)−.

Workup

  1. customquenched with acetic acid (0.5 mL)
  2. concentrationconcentrated
  3. customThe concentrate was purified by flash column chromatography (4:1 hexanes/ethyl acetate)

Sources & evidence

ORD record
ord-7dc871bed0e2437c8bf18ae7a00d2045
Source dataset
uspto-grants-2009_02
Patent number
US07491718B2

Reaction notes

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