Ethyl 4-nitrophenylacetate → 4-(2-Chloro-pyridin-4-ylmethyl)-phenylamine

HRID 729900Notes

Reaction equation

HRID 729900 reaction equation
FC(F)(F)C1C(CC2C=CC(N)=CC=2)=CC=CN=1.FC(F)(F)[C:21]1[CH:26]=[C:25]([CH2:27][C:28]2[CH:33]=[CH:32][C:31]([NH2:34])=[CH:30][CH:29]=2)[CH:24]=[CH:23][N:22]=1.C(OC(=O)CC1C=CC([N+]([O-])=O)=CC=1)C.[Cl:52]C1C=C([N+]([O-])=O)C=CN=1>>[Cl:52][C:21]1[CH:26]=[C:25]([CH2:27][C:28]2[CH:33]=[CH:32][C:31]([NH2:34])=[CH:30][CH:29]=2)[CH:24]=[CH:23][N:22]=1

Participants

5

Reactant 4

HCID 79517Ethyl 4-nitrophenylacetateHCID 7351522-Chloro-4-nitropyridineHCID 578335204-(2-Trifluoromethyl-pyridin-4-ylmethyl)-phenylamineHCID 689680904-(2-Trifluoromethyl-pyridinylmethyl)-phenylamine

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-pyridinylmethyl)-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-8bd4b8a20aa547c9901278ef3ce49d88
Source dataset
uspto-grants-2009_09
Patent number
US07582645B2

Reaction notes

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