Dipropan-2-yl(4-aminophenyl)phosphonate → 3-(5,5-Dimethyl-2-oxido-1,3,2-dioxaphosphinan-2-yl)aniline

HRID 511226Notes

Reaction equation

HRID 511226 reaction equation
NC1C=CC(P(=O)(OC(C)C)OC(C)C)=CC=1.[CH3:18][C:19]1([CH3:35])[CH2:24][O:23][P:22](=[O:34])([C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([N+:31]([O-])=O)[CH:26]=2)[O:21][CH2:20]1>>[CH3:18][C:19]1([CH3:35])[CH2:20][O:21][P:22]([C:25]2[CH:26]=[C:27]([CH:28]=[CH:29][CH:30]=2)[NH2:31])(=[O:34])[O:23][CH2:24]1

Participants

3

Reactant 2

HCID 86653993Dipropan-2-yl(4-aminophenyl)phosphonateHCID 866539965,5-Dimethyl-2-(3-nitrophenyl)-1,3,2-dioxaphosphinane 2-oxide

Product 1

HCID 866539953-(5,5-Dimethyl-2-oxido-1,3,2-dioxaphosphinan-2-yl)anilineYield 63%

Procedure

Prepared according to the procedure described for dipropan-2-yl (4-aminophenyl)phosphonate using 5,5-dimethyl-2-(3-nitrophenyl)-1,3,2-dioxaphosphinane 2-oxide. Yield: 63%. 1H-NMR (DMSO-d6, 400 MHz): δ=0.94 (s, 3 H), 1.07 (s, 3 H), 3.84 (dd, J=9.6, 10.8 Hz, 2 H), 4.07 (dd, J=11.2, 14.0 Hz, 2 H), 5.43 (s, br, 2 H), 6.75-6.78 (m, 2 H), 6.88 (d, 1 H), 7.16 (m, 1 H). MS: m/z 242.11 [MH+].

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-065d0393d93f46eebd17acd73b9a8b23
Source dataset
uspto-grants-2015_08
Patent number
US09096624B2

Reaction notes

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