4-Aminobenzonitrile → HCID 58636868, compound

HRID 1158986Notes

Reaction equation

[CH:1]1([C:4]2[N:9]=[C:8]([CH3:10])[C:7]3[O:11][C:12]([CH3:16])([CH3:15])[O:13][CH2:14][C:6]=3[C:5]=2[CH:17]=O)[CH2:3][CH2:2]1.[NH2:19][C:20]1[CH:27]=[CH:26][C:23]([C:24]#[N:25])=[CH:22][CH:21]=1>>[CH:1]1([C:4]2[C:5]([CH2:17][NH:19][C:20]3[CH:27]=[CH:26][C:23]([C:24]#[N:25])=[CH:22][CH:21]=3)=[C:6]3[CH2:14][O:13][C:12]([CH3:15])([CH3:16])[O:11][C:7]3=[C:8]([CH3:10])[N:9]=2)[CH2:2][CH2:3]1

Participants

Reactant 2

HCID 133964-Aminobenzonitrile

HCID 58636836HCID 58636836, compound

Product 1

HCID 58636868HCID 58636868, compoundYield 51.4%

Procedure

The reductive amination of 6-cyclopropyl-2,2,8-trimethyl-4H-[1,3]dioxino[4,5-c]pyridine-5-carbaldehyde (168) (5.11 g, 20.6 mmol) and 4-aminobenzonitrile (2.9 g, 24.7 mmol), as described in Example 21, gave give 4-[(6-cyclopropyl-2,2,8-trimethyl-4H-[1,3]dioxino[4,5-c]pyridin-5-ylmethyl)-amino]-benzonitrile (169) (3.7 g, 51% yield).

Workup

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Sources & evidence

ORD record: ord-4856e1ce31e44f508be6aac508821c00
Source dataset: uspto-grants-2010_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07812037B2

Reaction notes

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