Methyl 4-(bromomethyl)-3-methoxybenzoate → HCID 19744376, compound

HRID 358753Notes

Reaction equation

HRID 358753 reaction equation
[Cl:1][C:2]1[C:10]2[C:5](=[CH:6][C:7]([N+:11]([O-:13])=[O:12])=[CH:8][CH:9]=2)[N-:4][N:3]=1.[Na+].[CH3:15][O:16][C:17]1[CH:18]=[C:19]([CH:24]=[CH:25][C:26]=1[CH2:27]Br)[C:20]([O:22][CH3:23])=[O:21]>CO>[Cl:1][C:2]1[C:10]2[C:5](=[CH:6][C:7]([N+:11]([O-:13])=[O:12])=[CH:8][CH:9]=2)[N:4]([CH2:27][C:26]2[CH:25]=[CH:24][C:19]([C:20]([O:22][CH3:23])=[O:21])=[CH:18][C:17]=2[O:16][CH3:15])[N:3]=1

Participants

4

Reactant 2

HCID 2759828Methyl 4-(bromomethyl)-3-methoxybenzoateHCID 19744357HCID 19744357, compound

Product 1

HCID 19744376HCID 19744376, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 2.19 g. of sodium 3-chloro-6-nitroindazolide in 50 ml. methanol was stirred with 2.85 g methyl 3-methoxy-4-bromomethylbenzoate for 2 hours. After addition of 150 ml. water, the resultant precipitate was collected and recrystallised from ethyl acetate to give methyl 4-[3-chloro-6-nitroindazol-1-ylmethyl]-3-methoxybenzoate in 70% yield as a solid, m.p. 167°-168.5° C. A mixture of 1.25 g. of this solid was hydrogenated in the presence of 385 mg. 5% w/w palladium on calcium carbonate in 20 ml. ethyl acetate and 20 ml. methanol for 3 hours at a pressure of 1.1 bar. The catalyst was removed by filtration through diatomaceous earth. The filtrate was concentrated to low volume in vacuo and the residue (ca 3 ml.) was diluted with ether and petroleum ether (b.p. 40°-60° C.) and cooled to -20° C. The precipitated solid was collected and dried at 80° C. to give the ester L in 90% yield, m.p. 131°-131.5° C.

Workup

  1. additionA mixture of 2.19 g
  2. additionAfter addition of 150 ml
  3. customwater, the resultant precipitate was collected
  4. customrecrystallised from ethyl acetate

Sources & evidence

ORD record
ord-f75adee36b3b498baa11924aa6fd5831
Source dataset
uspto-grants-1991_03
Patent number
US04997844

Reaction notes

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