4-Bromo-2-nitroaniline → Benzenamine, 2-nitro-4-(2-propenyl)-

HRID 964609Notes

Reaction equation

Br[C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[C:4]([N+:9]([O-:11])=[O:10])[CH:3]=1.[CH2:12]([Sn](CCCC)(CCCC)CCCC)[CH:13]=[CH2:14].[K+].[Br-]>>[CH2:14]([C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[C:4]([N+:9]([O-:11])=[O:10])[CH:3]=1)[CH:13]=[CH2:12]

Participants

Reactant 3

HCID 701324-Bromo-2-nitroaniline

HCID 90628Allyltributylstannane

HCID 253877Potassium Bromide

Product 1

HCID 10329882Benzenamine, 2-nitro-4-(2-propenyl)-Yield 96%

Procedure

Prepared from 4-bromo-2-nitroaniline 17 (1.70 g, 7.84 mmol) and allyltributyltin (3.38 g, 10.2 mmol) as a yellow solid in 96% yield as described above for 5: mp 29°-31° C.; IR (KBr) 3490, 3374, 1638, 1518, 1341, 1253; 1H NMR δ7.90 (1H, d, J=2.0), 7.19 (1H, dd, J=8.5, 2.0), 6.77 (1H, d, J=8,5), 6.05 (NH, brs), 6.00-5.80 (1H, m), 5.11 (1H, dd, =1.4, 1.4), 5.04 (1H, ddd, J=6.6, 3.0, 1.5), 3.28 (1H, d, J=6.6); 13C NMR δ143.81, 137.13, 129.34, 125.59, 119.49, 116.95, 39.18; HRMS (EI) calcd for C9H10N2O2 178.0742, found 178.0746.

Sources & evidence

ORD record: ord-4e8e2cb0d688425a9c43b45332fa0259
Source dataset: uspto-grants-1998_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05770617

Reaction notes

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