Iodine → 8-nitro-2,3-dihydropyrano[3,2-e]isoindol-1(7H)-one

HRID 1727397Notes

Reaction equation

[C:1]1(=[O:14])[C:9]2[C:8]3[CH:10]=[CH:11][CH2:12][O:13][C:7]=3[CH:6]=[CH:5][C:4]=2[CH2:3][NH:2]1.[N:15]([O-:17])=[O:16].[Na+].II>CN1CCCC1.O>[N+:15]([C:11]1[CH2:12][O:13][C:7]2[CH:6]=[CH:5][C:4]3[CH2:3][NH:2][C:1](=[O:14])[C:9]=3[C:8]=2[CH:10]=1)([O-:17])=[O:16]

Participants

Conditions

Temperature: 0 °C

Procedure

To a mixture of 2,3-dihydropyrano[3,2-e]isoindol-1(7H)-one ((71) 2.3 g, 12.3 mmol) in N-methylpyrrolidine (150 ml) and H2O (3 ml) was added NaNO2 (3.4 g, 49.2 mmol) in portions. To the mixture cooled at 0° C. was added iodine (9.4 g, 36.9 mmol). The reaction mixture was stirred for 3 hr, then quenched with 58% NaHSO3 (12 ml), H2O (12 ml), followed by addition of another 30 ml of 58% NaHSO3 solution. The solid was participated, filtered, and washed with H2O. The desired compound was air-dried under vacuum to give the title compound (2.41 g, 84%) as a yellow solid. MS (ES) m/z 233.2.

Workup

customquenched with 58% NaHSO3 (12 ml), H2O (12 ml)
additionfollowed by addition of another 30 ml of 58% NaHSO3 solution
filtrationfiltered
washwashed with H2O
dry with materialThe desired compound was air-dried under vacuum

Sources & evidence

ORD record: ord-1c9d918f442245478de4033737cf8187
Source dataset: uspto-grants-2009_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07495111B2

Reaction notes

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