Stannous chloride dihydrate → 4-Chloro-N1-methyl-N1-phenylbenzene-1,2-diamine

HRID 16184Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]([CH3:15])[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[C:4]([N+:16]([O-])=O)[CH:3]=1.O.O.Cl[Sn]Cl>C(O)C>[Cl:1][C:2]1[CH:3]=[C:4]([NH2:16])[C:5]([N:8]([CH3:15])[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 40 °C

Procedure

To a solution of 4-chloro-N-methyl-2-nitro-N-phenylphenylamine (12.5 g, 46.3 mmol) in ethanol (250 mL) was added SnCl2.2H2O (37.5 gr., 0.17 mol). The solution was heated to 40° C. and stirred for 6 h. The reaction mixture was concentrated in vacuo and subsequently diluted with ethyl acetate (500 mL) and washed with H 20 (500 mL), a cooled (0° C.) aq. solution of NaOH (1 M, 200 mL), H2O (500 mL) and brine (500 mL). The organic layer was dried (Na2SO4), filtered and concentrated under reduced presssure. The crude compound was applied onto a silica column and eluted with heptane/ethyl acetate (8/2, v/v) affording the title compound (9.3 g, 87% yield). Data: Rf 0.65 (heptane/ethyl acetate, 7/3, v/v), (m/z)=233 (M+H)+.

Workup

concentrationThe reaction mixture was concentrated in vacuo
additionsubsequently diluted with ethyl acetate (500 mL)
washwashed with H 20 (500 mL)
temperaturea cooled (0° C.) aq. solution of NaOH (1 M, 200 mL), H2O (500 mL) and brine (500 mL)
dry with materialThe organic layer was dried (Na2SO4)
filtrationfiltered
concentrationconcentrated under reduced presssure
washeluted with heptane/ethyl acetate (8/2

Sources & evidence

ORD record: ord-bf03f142048549069bc2478ad7d6db48
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07737136B2

Reaction notes

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