2-[2-(9H-carbazol-1-ylamino)phenyl]propan-2-ol → 7,7-dimethyl-12,13-dihydro-7H-indolo[3,2-c]acridine

HRID 76380Notes

Reaction equation

[C:1]1([NH:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[C:21](O)([CH3:23])[CH3:22])[C:13]2[NH:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1>O>[CH3:22][C:21]1([CH3:23])[C:2]2[CH:3]=[CH:4][C:5]3[C:6]4[CH:7]=[CH:8][CH:9]=[CH:10][C:11]=4[NH:12][C:13]=3[C:1]=2[NH:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]1=2

Participants

Conditions

Temperature: 0 °C

Procedure

63 g (200 mmol) of 2-[2-(9H-carbazol-1-ylamino)phenyl]propan-2-ol are initially introduced in 268 g (2734 mmol) of polyphosphoric acid under protective gas and cooled to 0° C. The mixture is subsequently stirred at 100° C. for 3 h and then cooled to room temperature. Water is added to the mixture with ice cooling, the mixture is extracted with ethyl acetate, and the solvent is removed in vacuo. The content of product according to 1H-NMR is about 96% with an overall yield of 53 g (90%).

Workup

temperaturecooled to room temperature
extractionthe mixture is extracted with ethyl acetate
customthe solvent is removed in vacuo

Sources & evidence

ORD record: ord-6cee9cc7d498451f963df8108bf9e05c
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08835626B2

Reaction notes

Loading…