Phenol → HCID 9861815, compound

HRID 2186693Notes

Reaction equation

N(C(N(C)C)=O)=NC(N(C)C)=O.C([N:21]1[CH2:38][CH2:37][CH:25]2[N:26]3[C:35]4[C:30](=[CH:31][CH:32]=[CH:33][C:34]=4[CH:24]2[CH2:23][CH2:22]1)[CH:29]([OH:36])[CH2:28][CH2:27]3)(=O)C1C=CC=CC=1.[C:39]1(O)[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1.C(P(CCCC)CCCC)CCC>C1C=CC=CC=1>[O:36]([CH:29]1[C:30]2[C:35]3=[C:34]([C:24]4[CH2:23][CH2:22][NH:21][CH2:38][CH2:37][C:25]=4[N:26]3[CH2:27][CH2:28]1)[CH:33]=[CH:32][CH:31]=2)[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1

Participants

Conditions

Temperature: 60 °C

Procedure

1,1′-Azobis(N,N-dimethylformamide) (0.34 g, 2.0 mmol) was added to a solution of 10-benzoyl-5,6,8,9,10,11,12,12a-octahydro-4H,7aH-azepino[4′,5′:4,5]pyrrolo[3,2,1-ij]quinolin-4-ol (0.45 g, 1.3 mmol), phenol (0.18 g, 1.9 mmol), and tributylphosphine (0.49 mL, 2.0 mmol) in dry benzene (4.0 mL) at room temperature under N2. The reaction mixture immediately congealed but resumed stirring upon heating to 60° C. After 5 h, the reaction was cooled to room temperature and filtered to remove white precipitate. The filtrate was concentrated under reduced pressure and purified by silica gel chromatography with heptanes/EtOAc (gradient 3:1 to 3:2) to give 0.26 g (47%) of the title compound as a beige foam. 1H NMR (CDCl3) δ 7.52-7.38, 7.32, 7.11-6.95, 5.68, 4.21-3.90, 3.69, 3.21, 2.91, 2.63, 2.34; IR (drift) 1630, 1596, 1492, 1458, 1421, 1359, 1327, 1291, 1267, 1226, 1192, 786, 750, 706, 694 cm−1; MS (ESI) 423.3 (M++H).

Workup

temperaturethe reaction was cooled to room temperature
filtrationfiltered
customto remove white precipitate
concentrationThe filtrate was concentrated under reduced pressure
custompurified by silica gel chromatography with heptanes/EtOAc (gradient 3:1 to 3:2)

Sources & evidence

ORD record: ord-396a416b00bb44ddae5e3417f0f082ed
Source dataset: uspto-grants-2002_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06407092B1

Reaction notes

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