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

HRID 387692Notes

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), ammonium chloride (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 saline 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 saline in that order
dry with materialdried over sodium sulfate
concentrationconcentrated to dryness under reduced pressure

Sources & evidence

ORD record: ord-b640cbf0a01a4468bb3869a0c168edbc
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08372981B2

Reaction notes

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