Lithium hydroxide, monohydrate → 1-(cyanomethyl)-1H-indole-2-carboxylic acid

HRID 910651Notes

Reaction equation

HRID 910651 reaction equation
C([O:3][C:4]([C:6]1[N:7]([CH2:15][C:16]#[N:17])[C:8]2[C:13]([CH:14]=1)=[CH:12][CH:11]=[CH:10][CH:9]=2)=[O:5])C.O[Li].O>C1COCC1.O>[C:16]([CH2:15][N:7]1[C:8]2[C:13](=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:14]=[C:6]1[C:4]([OH:5])=[O:3])#[N:17]

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 713238ethyl 1-(cyanomethyl)-1H-indole-2-carboxylate

Product 1

HCID 64247931-(cyanomethyl)-1H-indole-2-carboxylic acidYield 70%

Reagents, catalysts & solvents 1

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

Procedure

To a solution of 1.0 eq. of 1-cyanomethyl-1H-indole-2-carboxylic acid ethyl ester in a mixture of THF/H2O ((9/1) was added LiOH.H2O (1.0 eq.) and the reaction mixture stirred 6 h at RT, 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 (70%).

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-63e6d2a73e1e4c2c805b3ee708c94e10
Source dataset
uspto-grants-2011_09
Patent number
US08022213B2

Reaction notes

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