Hydrochloric Acid → 4-(Benzyloxy)-5-fluoro-1H-indole-2-carboxylic acid

HRID 1404072Notes

Reaction equation

HRID 1404072 reaction equation
[CH2:1]([O:8][C:9]1[C:17]([F:18])=[CH:16][CH:15]=[C:14]2[C:10]=1[CH:11]=[C:12]([C:19]([O:21]C)=[O:20])[NH:13]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].Cl>>[CH2:1]([O:8][C:9]1[C:17]([F:18])=[CH:16][CH:15]=[C:14]2[C:10]=1[CH:11]=[C:12]([C:19]([OH:21])=[O:20])[NH:13]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 66927086Methyl 4-benzyloxy-5-fluoro-1H-indole-2-carboxylate

Product 1

HCID 669271414-(Benzyloxy)-5-fluoro-1H-indole-2-carboxylic acidYield 99%

Conditions

Temperature
85 °C

Procedure

Compound 1-3a was added to a solution of aqueous 2 N NaOH. The suspension was stirred at 80-90° C. until the reaction mixture became clear and was then held at reflux for 1-2 h. The solution was cooled and acidified with aqueous 3 N HCl, then the resulting precipitate was collected by filtration, washed with water, and dried under vacuum over P2O5 to provide the product (1-4a) in 99% yield. 1H NMR (CDCl3-d, 300 MHz) δ (ppm) 5.31 (s, 2H), 7.06-7.18 (m, 3H), 7.30-7.42 (m, 3H), 7.47-7.50 (m, 2H), 11.93 (bs, 1H).

Workup

  1. temperatureat reflux for 1-2 h
  2. temperatureThe solution was cooled
  3. filtrationthe resulting precipitate was collected by filtration
  4. washwashed with water
  5. dry with materialdried under vacuum over P2O5

Sources & evidence

ORD record
ord-849072df0ee14c8180f4d0edbc40215f
Source dataset
uspto-grants-2014_12
Patent number
US08912220B2

Reaction notes

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