1,2-Dichloroethane → 5-hydroxy-2-[(phenylmethyl)oxy]-N-3-pyridinylbenzamide

HRID 1623770Notes

Reaction equation

[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([NH2:7])[CH:2]=1.[OH:8][C:9]1[CH:10]=[CH:11][C:12]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[C:13]([CH:17]=1)[C:14](O)=[O:15].C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl>CN(C)C=O.O>[OH:8][C:9]1[CH:10]=[CH:11][C:12]([O:18][CH2:19][C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)=[C:13]([CH:17]=1)[C:14]([NH:7][C:3]1[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=1)=[O:15]

Participants

Conditions

Temperature: 25 °C

Procedure

3-Pyridinamine (2.20 g, 23.42 mmol) was added to a stirred solution of 5-hydroxy-2-[(phenylmethyl)oxy]benzoic acid (may be prepared as described in Description 76; 5.2 g, 21.29 mmol), HOBT (3.59 g, 23.4 mmol) and EDC (4.49 g, 23.42 mmol) in dimethylformamide (100 ml) at room temperature. The reaction mixture was stirred at 25° C. overnight. Water was added, the solid was filtered and washed with ethyl acetate to yield the title compound as a white solid. 3.7 g.

Workup

filtrationthe solid was filtered
washwashed with ethyl acetate

Sources & evidence

ORD record: ord-b9d54e571bbc41ddb481d1a2f6a94c3d
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08778939B2

Reaction notes

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