2-Chloro-4-nitropyridine → 4-(2-Chloro-pyridin-4-ylmethyl)-phenylamine

Reaction equation

FC(F)(F)[C:3]1[CH:8]=[C:7]([CH2:9][C:10]2[CH:15]=[CH:14][C:13]([NH2:16])=[CH:12][CH:11]=2)[CH:6]=[CH:5][N:4]=1.[Cl:19]C1C=C([N+]([O-])=O)C=CN=1>>[Cl:19][C:3]1[CH:8]=[C:7]([CH2:9][C:10]2[CH:15]=[CH:14][C:13]([NH2:16])=[CH:12][CH:11]=2)[CH:6]=[CH:5][N:4]=1

Participants

Reactant 2

HCID 7351522-Chloro-4-nitropyridine

HCID 578335204-(2-Trifluoromethyl-pyridin-4-ylmethyl)-phenylamine2×

Product 1

HCID 578334054-(2-Chloro-pyridin-4-ylmethyl)-phenylamine

Procedure

4-(2-Chloro-pyridin-4-ylmethyl)-phenylamine was prepared by a method analogous to that described for 4-(2-trifluoromethyl-pyridin-4-ylmethyl)-phenylamine (Intermediate 2P), starting from ethyl (4-nitrophenyl) acetate and 2-chloro-4-nitro-pyridine. 1H NMR (CHCl3-d) δ 8.23 (dd, J=5.1, 0.5 Hz, 1H), 7.11 (m, 1H), 7.01 (m, 1H), 6.95 (m, 2H), 6.65 (m, 2H), 3.83 (s, 2H).

Sources & evidence

ORD record: ord-2c816727f9b049af897f11c53087d718
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07582646B2

Reaction notes

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