Lithium hydroxide, monohydrate → HCID 59809687, compound

HRID 220624Notes

Reaction equation

HRID 220624 reaction equation
C([O:3][C:4]([C:6]1[N:7]([CH2:16][C:17]#[N:18])[C:8]2[C:13]([CH:14]=1)=[CH:12][C:11]([Cl:15])=[CH:10][CH:9]=2)=[O:5])C.O[Li].O>C1COCC1.O>[Cl:15][C:11]1[CH:12]=[C:13]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:16][C:17]#[N:18])[C:6]([C:4]([OH:5])=[O:3])=[CH:14]2

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 14595502HCID 14595502, compound

Product 1

HCID 59809687HCID 59809687, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

To a solution of 1.0 eq. of 5-chloro-1-cyanomethyl-1H-indole-2-carboxylic acid ethyl ester (prepared according to Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry (1989), 28B(12), 1065-8) in a mixture of THF/H2O ((9/1) was added LiOH.H2O (1.0 eq.) and the R/M stirred 6 h at R/T, acidified to pH2 and then partially concentrated until precipitation of the crude product which was filtered off and washed with Et2O and then dried to give the desired product as a light yellow solid (84%).

Workup

  1. concentrationpartially concentrated until precipitation of the crude product which
  2. filtrationwas filtered off
  3. washwashed with Et2O
  4. customdried

Sources & evidence

ORD record
ord-027386a50f304befa4de58863e8a037d
Source dataset
uspto-grants-2012_06
Patent number
US08202993B2

Reaction notes

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