Sodium Hydroxide → 7-Hydroxy-1.2,3,4-tetrahydro-4-quinolinone

HRID 1386413Notes

Reaction equation

C[O:2][C:3]1[CH:12]=[C:11]2[C:6]([C:7](=[O:13])[CH2:8][CH2:9][NH:10]2)=[CH:5][CH:4]=1.B(Br)(Br)Br.[OH-].[Na+]>C(Cl)Cl>[OH:2][C:3]1[CH:12]=[C:11]2[C:6]([C:7](=[O:13])[CH2:8][CH2:9][NH:10]2)=[CH:5][CH:4]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of 1.1 g (6.2 mmol) of 7-methoxy-1,2,3,4-tetrahydro-4-quinolinone (Rec. Trav. Chim., 1963;82:39) in 35 mL of CH2Cl2 was cooled in ice and treated with 5.0 mL of BBr3. After stirring at 0° C. for 0.5 hour, the solution was allowed to stir at room temperature overnight. The solution was poured into ice water and made basic with 50% NaOH. After extracting with Et2O, the pH was brought to 5.5 with dilute HCl, and the solution extracted twice with EtOAc. The EtOAc was washed with saturated NaCl and dried over MgSO4. Removal of the solvent under reduced pressure gave 0.5 g (49.5% yield) of the product as an orange solid. The structure was confirmed by NMR and mass spectroscopy. MS m/z 164 (M+H+).

Workup

stirringto stir at room temperature overnight
extractionAfter extracting with Et2O
extractionthe solution extracted twice with EtOAc
washThe EtOAc was washed with saturated NaCl
dry with materialdried over MgSO4
customRemoval of the solvent under reduced pressure

Sources & evidence

ORD record: ord-a5bb37aae2be4c13af6cce1db2005d52
Source dataset: uspto-grants-2001_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06265422B1

Reaction notes

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