Ethanol → 4-(4-Aminophenoxy)-7-(benzyloxy)-6-cyanoquinoline

HRID 853212Notes

Reaction equation

[Cl-].[NH4+].C(O)C.[CH2:6]([O:13][C:14]1[CH:23]=[C:22]2[C:17]([C:18]([O:24][C:25]3[CH:30]=[CH:29][C:28]([N+:31]([O-])=O)=[CH:27][CH:26]=3)=[CH:19][CH:20]=[N:21]2)=[CH:16][C:15]=1[C:34]#[N:35])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1>[Fe].O>[NH2:31][C:28]1[CH:27]=[CH:26][C:25]([O:24][C:18]2[C:17]3[C:22](=[CH:23][C:14]([O:13][CH2:6][C:7]4[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=4)=[C:15]([C:34]#[N:35])[CH:16]=3)[N:21]=[CH:20][CH:19]=2)=[CH:30][CH:29]=1

Participants

Conditions

Temperature: 90 °C

Procedure

Iron powder (0.6 g), ammoniumchloride (1.4 g), ethanol (100 ml) and water (30 ml) were added to the 7-benzyloxy-6-cyano-4-(4-nitrophenoxy)quinoline obtained in Production Example 5, and the mixture was stirred at 90° C. for 2.5 hours. The reaction system was returned to room temperature and then filtered with celite, the filtrate was subjected to liquid separation, and the organic layer was washed with water and saturated brine in that order, dried over sodium sulfate and then concentrated to dryness under reduced pressure to obtain 1.31 g of a crude product containing the target substance. The crude product was used directly for the following reaction. (Production Example 7).

Workup

customobtained in Production Example 5
customwas returned to room temperature
filtrationfiltered with celite
customthe filtrate was subjected to liquid separation
washthe organic layer was washed with water and saturated brine in that order
dry with materialdried over sodium sulfate
concentrationconcentrated to dryness under reduced pressure

Sources & evidence

ORD record: ord-ab91773db30a4cd7b6267ede387bda06
Source dataset: uspto-grants-2007_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07253286B2

Reaction notes

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