Isopropyl iodide → 2-Methyl-7-nitro-4-(propan-2-yloxy)-2,3-dihydro-1H-isoindol-1-one

HRID 511446Notes

Reaction equation

HRID 511446 reaction equation
CO[C:3]1[CH:11]=CC([N+]([O-])=O)=C2[C:4]=1CN(C)C2=O.[OH:17][C:18]1[CH:26]=[CH:25][C:24]([N+:27]([O-:29])=[O:28])=[C:23]2[C:19]=1[CH2:20][N:21]([CH3:31])[C:22]2=[O:30].C(I)(C)C>>[CH3:31][N:21]1[CH2:20][C:19]2[C:23](=[C:24]([N+:27]([O-:29])=[O:28])[CH:25]=[CH:26][C:18]=2[O:17][CH:3]([CH3:11])[CH3:4])[C:22]1=[O:30]

Participants

4

Reactant 3

HCID 6362Isopropyl iodideHCID 598491794-Methoxy-2-methyl-7-nitro-2,3-dihydro-isoindol-1-one2×HCID 598492054-Hydroxy-2-methyl-7-nitro-2,3-dihydro-isoindol-1-one3×

Product 1

HCID 672547622-Methyl-7-nitro-4-(propan-2-yloxy)-2,3-dihydro-1H-isoindol-1-one

Procedure

The title compound was prepare according to the procedure for 4-Methoxy-2-methyl-7-nitro-2,3-dihydro-1H-isoindol-1-one (Compound 205B) using 4-Hydroxy-2-methyl-7-nitro-2,3-dihydro-1H-isoindol-1-one and 4-Hydroxy-2-methyl-7-nitro-2,3-dihydro-1H-isoindol-1-one (Compound 205C, 50.0 mg, 0.240 mmol) and isopropyl iodide. 1H NMR (400 MHz, CD3OD) δ=1.40 (d, J=6.1 Hz, 6 H), 3.15 (s, 3 H), 4.37 (s, 2 H), 4.80-4.87 (m, 1 H), 7.22 (d, J=8.8 Hz, 1 H), 7.86 (d, J=8.8 Hz, 1 H). MS (ES+): m/z 237.18 (100) [MH+]; HPLC: tR=0.94 min (UPLC, Analytical).

Sources & evidence

ORD record
ord-b6552d398aac48b4938d917f955b4373
Source dataset
uspto-grants-2015_08
Patent number
US09096624B2

Reaction notes

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