Sodium Hydroxide → 7-Bromo-3-chloro-5',6'-dihydrospiro[chromeno[2,3-c]pyridine-5,4'-[1,3]thiazin]-2'-amine

HRID 455611Notes

Reaction equation

[OH-].[Na+].Cl.[Br:4][C:5]1[CH:6]=[C:7]2[C:18]3([CH2:23][CH2:22][S:21][C:20]([NH:24]C(=O)C4C=CC([N+]([O-])=O)=CC=4)=[N:19]3)[C:17]3[CH:16]=[C:15]([Cl:36])[N:14]=[CH:13][C:12]=3[O:11][C:8]2=[CH:9][CH:10]=1>CO.O>[Br:4][C:5]1[CH:6]=[C:7]2[C:18]3([CH2:23][CH2:22][S:21][C:20]([NH2:24])=[N:19]3)[C:17]3[CH:16]=[C:15]([Cl:36])[N:14]=[CH:13][C:12]=3[O:11][C:8]2=[CH:9][CH:10]=1

Participants

Conditions

Temperature: 65 °C

Procedure

A 2 N NaOH solution (24.47 ml, 48.9 mmol) was added to a solution of N-(7-bromo-3-chloro-5′,6′-dihydrospiro[chromeno[2,3-c]pyridine-5,4′-[1,3]thiazin]-2′-yl)-4-nitrobenzamide hydrochloride (9.5 g, 16.32 mmol) in MeOH (250 ml). The reaction mixture was heated to 65° C. for 3 hours. The reaction mixture was diluted with water (300 mL), stirred for 10 min, and then filtered. The solid was washed with water and dried under reduced pressure to afford 7-bromo-3-chloro-5′,6′-dihydrospiro[chromeno[2,3-c]pyridine-5,4′-[1,3]thiazin]-2′-amine (3.9 g, 9.83 mmol, 60.3% yield).

Workup

filtrationfiltered
washThe solid was washed with water
customdried under reduced pressure

Sources & evidence

ORD record: ord-ff72366517ef4635bbec84cefb0d76bb
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08497264B2

Reaction notes

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