Methyl 4-(bromomethyl)-3-methoxybenzoate → HCID 178497911, compound

HRID 275146Notes

Reaction equation

HRID 275146 reaction equation
[N+:1]([C:4]1[CH:12]=[C:11]2[C:7]([C:8]([OH:13])=[N:9][NH:10]2)=[CH:6][CH:5]=1)([O-:3])=[O:2].[Na].Br[CH2:16][C:17]1[CH:26]=[CH:25][C:20]([C:21]([O:23][CH3:24])=[O:22])=[CH:19][C:18]=1[O:27][CH3:28]>CO.CN(C)C=O.C(OCC)(=O)C>[OH:13][C:8]1[C:7]2[C:11](=[CH:12][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=2)[N:10]([CH2:16][C:17]2[CH:26]=[CH:25][C:20]([C:21]([O:23][CH3:24])=[O:22])=[CH:19][C:18]=2[O:27][CH3:28])[N:9]=1

Participants

7

Reactant 3

HCID 2759828Methyl 4-(bromomethyl)-3-methoxybenzoateHCID 5360545SodiumHCID 178526464HCID 178526464, compound

Product 1

HCID 178497911HCID 178497911, compoundYield 38.5%

Reagents, catalysts & solvents 3

HCID 887MethanolSolvent2×HCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

6-Nitroindazolol (0.206 g.) was added to a solution of sodium (0.026 g.) in methanol (1.5 ml.), and the mixture heated at 50° C. for 10 minutes. A solution of methyl 4-bromomethyl-3-methoxybenzoate (B) (0.327 g.) in methanol (3.75 ml.) and N,N-dimethylformamide (DMF) (1.25 ml.) was added, and the mixture was refluxed for 18 hours. The cooled mixture was diluted with ethyl acetate and DMF, and washed with water and brine, then dried (MgSO4) and evaporated. The residue was triturated with 1:1 v/v ethyl acetate:ether to give methyl 4-[3-hydroxy-6-nitroindazol-1-ylmethyl]-3-methoxybenzoate (T) (0.158 g., 38%) as a yellow solid, m.p. 231°-235° C.

Workup

  1. temperaturethe mixture was refluxed for 18 hours
  2. washwashed with water and brine
  3. dry with materialdried (MgSO4)
  4. customevaporated
  5. customThe residue was triturated with 1:1 v/v ethyl acetate

Sources & evidence

ORD record
ord-06b10746e3d54c19bf26ec11ee446aef
Source dataset
uspto-grants-1995_02
Patent number
US05391758

Reaction notes

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