Sodium Hydroxide → HCID 22310877, compound

HRID 2305581Notes

Reaction equation

HRID 2305581 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:20]=[CH:21][CH:22]=1)[CH2:5][N:6]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:8]=[C:7]1[C:15]([O:17]CC)=[O:16].[OH-].[Na+]>C1COCC1.CO>[Cl:1][C:2]1[CH:3]=[C:4]([CH:20]=[CH:21][CH:22]=1)[CH2:5][N:6]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:8]=[C:7]1[C:15]([OH:17])=[O:16]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 22310997HCID 22310997, compound

Product 1

HCID 22310877HCID 22310877, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

Ethyl N-(3-chlorobenzyl)indole-2-carboxylate (0.47 g) was dissolved in THF/MeOH (1:1) and sodium hydroxide (2M, 4.5 ml) was added and the reaction stirred for 16 hours. The reaction was then concentrated in vacuo to dryness and the residue dissolved in water. The solution was acidified to pH 3 by dropwise addition of acetic acid, resulting in the precipitation of a white solid which was filtered off, washed with water and dried in vacuo to give the desired end product (0.35 g, 82%), mp 188-189°; NMR δ(CD3SOCD3) 5.85 (s, 2H), 6.90 (d, 1H), 7.1 (m, 2H), 7.3 (m, 4H), 7.55 (d, 1H), 7.70 (d, 1H); M/z (−) 284 (M−H+).

Workup

  1. concentrationThe reaction was then concentrated in vacuo to dryness
  2. dissolutionthe residue dissolved in water
  3. additionThe solution was acidified to pH 3 by dropwise addition of acetic acid
  4. customresulting in the precipitation of a white solid which
  5. filtrationwas filtered off
  6. washwashed with water
  7. customdried in vacuo

Sources & evidence

ORD record
ord-d3607d1069ed4170b8535d362c3396ed
Source dataset
uspto-grants-2002_08
Patent number
US06441004B1

Reaction notes

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