Lithium hydroxide, monohydrate → HCID 22638693, compound

HRID 2416261Notes

Reaction equation

HRID 2416261 reaction equation
C([O:3][C:4]([CH:6]1[CH2:8][CH:7]1[CH2:9][C:10]1[CH:11]=[C:12]2[C:16](=[CH:17][CH:18]=1)[NH:15][CH:14]=[C:13]2[C:19]#[N:20])=[O:5])C.O.[OH-].[Li+]>CO>[C:19]([C:13]1[C:12]2[C:16](=[CH:17][CH:18]=[C:10]([CH2:9][CH:7]3[CH2:8][CH:6]3[C:4]([OH:5])=[O:3])[CH:11]=2)[NH:15][CH:14]=1)#[N:20]

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 67551142HCID 67551142, compound

Product 1

HCID 22638693HCID 22638693, compoundYield 81.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2-(3-Cyano-1H-indol-5-ylmethyl)-cyclopropanecarboxylic acid ethyl ester (0.62 g, 2.31 mmol), methanol (10 ml), and lithium hydroxide monohydrate (0.48 g, 11.6 mmol) were heated at a gentle reflux for 2 h. The solution was concentrated in vacuo and the residue taken up in 1 N hydrochloric acid (30 ml) and extracted with ethyl acetate (3×10 ml). The combined organic extracts were dried over anhydrous sodium sulfate and concentrated in vacuo to afford 2-(3-Cyano-1H-indol-5-ylmethyl)-cyclopropanecarboxylic acid (0.45 g, 81%) as a light brown oil which solidified upon standing. LC-MS: 1.21 min; 263.2 (MNa)+.

Workup

  1. temperaturea gentle reflux for 2 h
  2. concentrationThe solution was concentrated in vacuo
  3. extractionextracted with ethyl acetate (3×10 ml)
  4. dry with materialThe combined organic extracts were dried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-831fd4b53236415db1def34933d6a530
Source dataset
uspto-grants-2004_11
Patent number
US06822100B2

Reaction notes

Loading…