Methanol → HCID 19744393, compound

HRID 358748Notes

Reaction equation

HRID 358748 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][C:12]=1[CH2:13][N:14]1[C:22]2[C:17](=[CH:18][CH:19]=[C:20]([N+:23]([O-:25])=[O:24])[CH:21]=2)[CH:16]=[CH:15]1)[C:6]([O:8]C)=[O:7].CO.C1COCC1.O.[OH-].[Li+]>O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][C:12]=1[CH2:13][N:14]1[C:22]2[C:17](=[CH:18][CH:19]=[C:20]([N+:23]([O-:25])=[O:24])[CH:21]=2)[CH:16]=[CH:15]1)[C:6]([OH:8])=[O:7]

Participants

6

Reactant 4

HCID 887MethanolHCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 14708760HCID 14708760, compound

Product 1

HCID 19744393HCID 19744393, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Nitrogen was passed through a solution containing 1.39 g. methyl 3-methoxy-4-(6-nitroindol-1-ylmethyl)benzoate in 1:1 v/v methanol and THF together with 0.86 g. lithium hydroxide monohydrate in 25 ml. water. After 1 minute the reaction mixture was sealed and stirred for 3 days. Solvent was then evaporated. The residue was diluted with water, acidified (1 M hydrochloric acid) and extracted with ethyl acetate. The extracts were washed with water, then with brine and were dried (MgSO4) Evaporation of solvent gave a 3-methoxy-4-[6-nitroindol-1-ylmethyl]benzoic acid in 91% yield as a solid m.p. 243°-245.5° C. which was used without further purification.

Workup

  1. additioncontaining 1.39 g
  2. customAfter 1 minute the reaction mixture was sealed
  3. customSolvent was then evaporated
  4. additionThe residue was diluted with water
  5. extractionextracted with ethyl acetate
  6. washThe extracts were washed with water
  7. dry with materialwith brine and were dried
  8. custom(MgSO4) Evaporation of solvent

Sources & evidence

ORD record
ord-5e4e2d5a566a4ad6a79503be57a638f2
Source dataset
uspto-grants-1991_03
Patent number
US04997844

Reaction notes

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