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

HRID 511225Notes

Reaction equation

HRID 511225 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][C:28]([N+:31]([O-])=O)=[CH:27][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:30]=[CH:29][C:28]([NH2:31])=[CH:27][CH:26]=2)(=[O:34])[O:23][CH2:24]1

Participants

3

Reactant 2

HCID 86653993Dipropan-2-yl(4-aminophenyl)phosphonateHCID 866539945,5-Dimethyl-2-(4-nitrophenyl)-1,3,2-dioxaphosphinane 2-oxide

Product 1

HCID 154263354-(5,5-Dimethyl-2-oxido-1,3,2-dioxaphosphinan-2-yl)anilineYield 41%

Procedure

Prepared according to the procedure described for dipropan-2-yl (4-aminophenyl)phosphonate using 5,5-dimethyl-2-(4-nitrophenyl)-1,3,2-dioxaphosphinane 2-oxide. Yield: 41%. 1H-NMR (DMSO-d6, 400 MHz): δ=0.97 (s, 3 H), 1.02 (s, 3 H), 3.78 (m, 2 H), 4.08 (m, 2 H), 5.91 (s, br, 2 H), 6.61 (dd, J=3.6, 8.4 Hz, 2 H), 7.34 (m, 2 H). MS: m/z 242.10 [MH+].

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-12509e46aafe4b74b095a225b92535b0
Source dataset
uspto-grants-2015_08
Patent number
US09096624B2

Reaction notes

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