Sodium Hydroxide → HCID 66680432, compound

HRID 1753922Notes

Reaction equation

HRID 1753922 reaction equation
C([O:3][C:4]([CH:6]1[C:18]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][C:16]=3[O:19][CH3:20])[N:11]([CH2:21][CH2:22][F:23])[C:10]=2[CH2:9][CH2:8][CH2:7]1)=[O:5])C.[OH-].[Na+]>C(O)C.O>[F:23][CH2:22][CH2:21][N:11]1[C:10]2[CH2:9][CH2:8][CH2:7][CH:6]([C:4]([OH:5])=[O:3])[C:18]=2[C:17]2[C:12]1=[CH:13][CH:14]=[CH:15][C:16]=2[O:19][CH3:20]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 66679520HCID 66679520, compound

Product 1

HCID 66680432HCID 66680432, compoundYield 99.3%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

8-chloro-9-(2-Fluoroethyl)-5-methoxy-2,3,4,9-tetrahydro-1H-carbazole-4-carboxylic acid ethyl ester (16) (380 mg, 1.2 mmol) was dissolved in ethanol (4 mL). A solution of sodium hydroxide (580 mg, 14.5 mmol) dissolved in 6 mL of water, was added. The reaction mixture was heated to reflux overnight. The solvent was removed in vacuo and the crude mixture diluted with water, acidified with 2 N HCl until acidic, and washed with dichloromethane. The organics were combined and dried over magnesium sulfate and concentrated in vacuo to give 347 mg (quantitative) of 9-(2-Fluoroethyl)-5-methoxy-2,3,4,9-tetrahydro-1H-carbazole-4-carboxylic acid (17) as an off white solid which was used crude into the next step. The structure was confirmed by 13C NMR (75 MHz; CDCl3): δC 20.4, 21.9, 27.2, 39.9, 43.3 (d, JCF=23 Hz), 55.1, 81.9 (d, JCF=173 Hz), 100.3, 102.8, 106.2, 117.1, 122.2, 135.6, 137.8, 153.3, and 180.8.

Workup

  1. additionwas added
  2. temperatureThe reaction mixture was heated
  3. temperatureto reflux overnight
  4. customThe solvent was removed in vacuo
  5. additionthe crude mixture diluted with water
  6. washwashed with dichloromethane
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-27495513f4264758b48def651f3935aa
Source dataset
uspto-grants-2015_10
Patent number
US09168317B2

Reaction notes

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