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Sodium Hydroxide → 3-chloro-4-fluoro-1-methyl-1H-indole-5-carboxylic acid

HRID 1053846
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1053846
[Cl:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:12]([O:14]C)=[O:13])[C:9]=2[F:11])[N:4]([CH3:16])[CH:3]=1.[OH-].[Na+]>O1CCCC1.CO.ClCCl>[Cl:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:12]([OH:14])=[O:13])[C:9]=2[F:11])[N:4]([CH3:16])[CH:3]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 2

HCID 14798Sodium Hydroxide2×HCID 90014771methyl 3-chloro-4-fluoro-1-methyl-1H-indole-5-carboxylate

Produkt 1

HCID 900232723-chloro-4-fluoro-1-methyl-1H-indole-5-carboxylic acid

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 887MethanolLösungsmittelHCID 6344DichloromethaneLösungsmittel
HCID 8028
Tetrahydrofuran
Lösungsmittel

Versuchsvorschrift

The ester thus obtained was dissolved in a mixture of tetrahydrofuran (10 mL), methanol (10 mL) and dichloromethane (3 mL). 2 M sodium hydroxide (4.31 mL) was added and the mixture stirred at room temperature for 3 h. Further 2 M sodium hydroxide (4.31 mL) was added and the reaction stirred at room temperature for 16 h. The mixture was concentrated in vacuo, diluted with water and ethyl acetate added. The resultant emulsion was acidified with 1 M hydrochloric acid (pH=2-3) and extracted with ethyl acetate. The combined ethyl acetate phases were dried and concentrated to give the title compound (0.274 g) as a pale yellow solid.

Aufarbeitung

  1. stirringthe reaction stirred at room temperature for 16 h
  2. concentrationThe mixture was concentrated in vacuo
  3. additiondiluted with water and ethyl acetate
  4. additionadded
  5. extractionextracted with ethyl acetate
  6. dry with materialThe combined ethyl acetate phases were dried
  7. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-2dc5e20b92294d31bf735bb6f93d6faa
Quelldatensatz
uspto-grants-2016_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09394250B2

Notizen zur Reaktion

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