Phenol → HCID 9861815, compound

HRID 1813910Notes

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]quinoline-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-73acf580f4014026ba34c444be90ab3d
Source dataset: uspto-grants-2005_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06875762B2

Reaction notes

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