Water → 1H,3H,4H-Pyrrolo[2,1-c][1,4]oxazine-8-carboxylic acid

HRID 926363

Reaktionsgleichung

Reaktionsgleichung von HRID 926363
C([O:3][C:4]([C:6]1[CH:7]=[CH:8][N:9]2[CH2:14][CH2:13][O:12][CH2:11][C:10]=12)=[O:5])C.O.[OH-].[Na+]>CO>[CH2:11]1[C:10]2=[C:6]([C:4]([OH:5])=[O:3])[CH:7]=[CH:8][N:9]2[CH2:14][CH2:13][O:12]1

Komponenten

5

Edukt 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 897268463,4-dihydro-1H-pyrrolo[2,1-c][1,4]oxazine-8-carboxylic acid ethyl ester

Produkt 1

HCID 825972611H,3H,4H-Pyrrolo[2,1-c][1,4]oxazine-8-carboxylic acidAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

To a solution of 3,4-dihydro-1H-pyrrolo[2,1-c][1,4]oxazine-8-carboxylic acid ethyl ester (Comp. No. 2a) (3.2 g, 16.4 mmol) in methanol (64 ml) was added water (64 ml) and sodium hydroxide (3.3 g, 82 mmol) and the mixture was stirred at reflux until complete conversion according to LC/MC (about 4 h). Approximately half of the solvents were evaporated in vacuo and the mixture was acidified with excess hydrochloric acid. The forming precipitate was filtered off, washed once with water and dried in vacuo to give 2.7 g (100%) of 3,4-dihydro-1H-pyrrolo[2,1-c][1,4]oxazine-8-carboxylic acid as white solid. LC/MS (method 4): Rt=0.77 min; m/z=168.02 (M+H+).

Aufarbeitung

  1. temperatureat reflux until complete conversion
  2. customaccording to LC/MC (about 4 h)
  3. customApproximately half of the solvents were evaporated in vacuo
  4. filtrationThe forming precipitate was filtered off
  5. washwashed once with water
  6. customdried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-951b45902add4d0b88cbc51240449200
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09284333B2

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