Water → 2-Chloro-5-nitro-N-{4-[(phenylmethyl)oxy]phenyl}-4-pyridineamine

HRID 1986379Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[C:6](Cl)[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][N:3]=1.Cl.[CH2:13]([O:20][C:21]1[CH:27]=[CH:26][C:24]([NH2:25])=[CH:23][CH:22]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.CCN(CC)CC.O>CN(C=O)C>[Cl:1][C:2]1[CH:7]=[C:6]([NH:25][C:24]2[CH:23]=[CH:22][C:21]([O:20][CH2:13][C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=3)=[CH:27][CH:26]=2)[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][N:3]=1

Participants

Conditions

Temperature: 60 °C

Procedure

The product of Example 1, Step 3 (15.2 g, 78.7 mmol), 4-benzyloxyaniline HCl (15.6 g, 78.7 mmol) and Et3N (27 mL, 196.9 mmol) were combined in DMF (125 mL) and heated to 60° C. for 1 h. The reaction mixture was cooled and H2O (200 mL) was added dropwise over 1 h. The resulting yellow/orange precipitate was filtered and washed with Et2O to provide the title compound as a yellow powder (25.8 g, 92%). MS (ES+) m/e 356 [M+H]+.

Workup

temperatureThe reaction mixture was cooled
filtrationThe resulting yellow/orange precipitate was filtered
washwashed with Et2O

Sources & evidence

ORD record: ord-ee1afc2dcdc046a6a1b5abdfa073d197
Source dataset: uspto-grants-2009_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07547779B2

Reaction notes

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