Lithium hydroxide, monohydrate → HCID 59375023, compound

HRID 1811103Notes

Reaction equation

HRID 1811103 reaction equation
[C:1]([C:4]1[CH:5]=[CH:6][C:7]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[F:28])=[C:8]2[C:16]=1[NH:15][C:14]1[CH:13]=[C:12]([C:17]([O:19]CC)=[O:18])[CH:11]=[CH:10][C:9]2=1)(=[O:3])[NH2:2].O.[OH-].[Li+]>C1COCC1.C(O)C.O>[C:1]([C:4]1[CH:5]=[CH:6][C:7]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[F:28])=[C:8]2[C:16]=1[NH:15][C:14]1[CH:13]=[C:12]([C:17]([OH:19])=[O:18])[CH:11]=[CH:10][C:9]2=1)(=[O:3])[NH2:2]

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 59375158HCID 59375158, compound

Product 1

HCID 59375023HCID 59375023, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 18504229Ethanol tetrahydrofuran waterSolvent

Procedure

A suspension of ethyl 8-carbamoyl-5-(2-fluorophenyl)-9H-carbazole-2-carboxylate (Example 3-12, 0.8 g, 2.126 mmol) and lithium hydroxide monohydrate (0.255 g, 6.38 mmol) in THF-ethanol-water (3:1:1) (25.0 mL) was heated at reflux for 4 h. The mixture was concentrated and the residue was suspended in water. The pH was adjusted to 1-2 by addition of 1 M hydrochloric acid. The precipitate was collected by filtration, washed with water and dried to provide 8-carbamoyl-5-(2-fluorophenyl)-9H-carbazole-2-carboxylic acid as a yellow solid (520 mg, 71%). 1H NMR (400 MHz, DMSO-d6) δ 12.77 (br. s., 1 H) 11.87 (s, 1 H) 8.41 (m, 1 H) 8.26 (br. s., 1 H) 8.08 (d, J=7.69 Hz, 1 H) 7.50-7.67 (m, 4 H) 7.40-7.49 (m, 2 H) 7.09-7.17 (m, 2 H). Mass spectrum m/z 349.1 (M+H)+.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 4 h
  3. concentrationThe mixture was concentrated
  4. additionThe pH was adjusted to 1-2 by addition of 1 M hydrochloric acid
  5. filtrationThe precipitate was collected by filtration
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-b15b21c1ab634a9c893ab6f99166db53
Source dataset
uspto-grants-2013_01
Patent number
US08362065B2

Reaction notes

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