Hydrochloric Acid → Methyl 4-[5-(formylmethyl)-1-propylindol-3-ylmethyl]-3-methoxybenzoate

HRID 2248776Notes

Reaction equation

HRID 2248776 reaction equation
C[O:2][CH:3](OC)[CH2:4][C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[N:10]([CH2:14][CH2:15][CH3:16])[CH:9]=[C:8]2[CH2:17][C:18]1[CH:27]=[CH:26][C:21]([C:22]([O:24][CH3:25])=[O:23])=[CH:20][C:19]=1[O:28][CH3:29].Cl>O1CCCC1>[CH:3]([CH2:4][C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[N:10]([CH2:14][CH2:15][CH3:16])[CH:9]=[C:8]2[CH2:17][C:18]1[CH:27]=[CH:26][C:21]([C:22]([O:24][CH3:25])=[O:23])=[CH:20][C:19]=1[O:28][CH3:29])=[O:2]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 19995020HCID 19995020, compound

Product 1

HCID 19994986Methyl 4-[5-(formylmethyl)-1-propylindol-3-ylmethyl]-3-methoxybenzoate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of methyl 4-[5-(2,2-dimethoxyethyl)-1-propylindol-3-ylmethyl]-3-methoxybenzoate (0.46 g) in tetrahydrofuran (7 ml) and b 1M hydrochloric acid (3.6 ml) was stirred at ambient temperature for 11 h, under a nitrogen atmosphere. The mixture was poured onto water, extracted with ethyl acetate (twice), and the extract washed with water (twice), brine, and then dried (MgSO4). The solvent was evaporated to give a dark oil which was used in the next step without further purification.

Workup

  1. additionThe mixture was poured onto water
  2. extractionextracted with ethyl acetate (twice), and the extract
  3. washwashed with water (twice), brine
  4. dry with materialdried (MgSO4)
  5. customThe solvent was evaporated
  6. customto give a dark oil which
  7. customwas used in the next step without further purification

Sources & evidence

ORD record
ord-57f97e53e3f847eb9370a42b701a2b47
Source dataset
uspto-grants-1991_08
Patent number
US05041460

Reaction notes

Loading…