Tetrafluoroboric acid → HCID 15869798, compound

HRID 1602602Notes

Reaction equation

N[C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][CH2:7][N:8]2[C:11](=[O:15])[CH2:12][CH2:13][Cl:14])=[CH:4][CH:3]=1.N([O-])=O.[Na+].[H+].[B-](F)(F)(F)[F:22]>Cl.O>[Cl:14][CH2:13][CH2:12][C:11]([N:8]1[C:9]2[C:5](=[CH:4][CH:3]=[C:2]([F:22])[CH:10]=2)[CH2:6][CH2:7]1)=[O:15]

Participants

Conditions

Temperature: 10 °C

Procedure

1.12 g (5.0 mmol) of 6-amino-1-(3-chloropropionyl)indoline (prepared as described in Preparation 6) were suspended in 20 ml of 6 N aqueous hydrochloric acid, and a solution of 380 mg (5.5 mmol) of sodium nitrite in 5 ml of water was added to the suspension while ice-cooling so that the internal temperature was maintained at 10° C. or lower. The mixture was then stirred while ice-cooling for 30 minutes. At the end of this time, 2.0 mg (8.4 mmol) of fluoboric acid (as a 42% w/v aqueous solution) were added to the mixture, and the resulting mixture was stirred at 0° C. for 1 hour. The precipitated salt was collected by filtration. This salt was dried over phosphorous pentoxide in a desiccator under reduced pressure by means of a vacuum pump overnight to obtain 1.23 g (3.8 mmol) of the title compound as a solid (yield: 76%).

Workup

temperaturecooling so that the internal temperature
temperaturecooling for 30 minutes
stirringthe resulting mixture was stirred at 0° C. for 1 hour
filtrationThe precipitated salt was collected by filtration
dry with materialThis salt was dried over phosphorous pentoxide in a desiccator under reduced pressure by means of a vacuum pump overnight

Sources & evidence

ORD record: ord-4d7046c4b2df403f940b88a5185320d7
Source dataset: uspto-grants-1999_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05981752

Reaction notes

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