Acetic Acid → HCID 22291028, compound

HRID 1369553Notes

Reaction equation

[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:25])[C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([N:16]3[CH2:21][CH2:20][O:19][CH2:18][CH2:17]3)[C:11]=2[N+:22]([O-])=O)=[CH:4][C:3]=1[NH:26][C:27](=[O:40])[C:28]1[CH:33]=[CH:32][C:31]([CH2:34][N:35]([CH2:38][CH3:39])[CH2:36][CH3:37])=[CH:30][CH:29]=1.C(O)(=O)C.O.C(=O)(O)[O-].[Na+]>[Fe].C(O)C>[NH2:22][C:11]1[C:12]([N:16]2[CH2:21][CH2:20][O:19][CH2:18][CH2:17]2)=[CH:13][CH:14]=[CH:15][C:10]=1[C:9]([NH:8][C:5]1[CH:6]=[CH:7][C:2]([CH3:1])=[C:3]([NH:26][C:27](=[O:40])[C:28]2[CH:29]=[CH:30][C:31]([CH2:34][N:35]([CH2:38][CH3:39])[CH2:36][CH3:37])=[CH:32][CH:33]=2)[CH:4]=1)=[O:25]

Participants

Conditions

Temperature: 95 °C

Procedure

A mixture of N-[2-methyl-5-(3-morpholino-2-nitrobenzamido)phenyl]-4-diethylaminomethylbenzamide (1.21 g), iron powder (1.24 g), glacial acetic acid (0.44 ml), water (2.2 ml) and ethanol (22.2 ml) was stirred and heated to 95° C. for 9 hours. The resultant mixture was cooled to ambient temperature and basified to pH9 by the addition of a saturated aqueous sodium bicarbonate solution. The mixture was filtered and the filtrate was evaporated. The residue was partitioned between ethyl acetate and a saturated aqueous sodium bicarbonate solution. The organic phase was dried (MgSO4) and evaporated. There was thus obtained the title compound as a solid (0.826 g); Mass Spectrum: M+H+516.

Workup

filtrationThe mixture was filtered
customthe filtrate was evaporated
customThe residue was partitioned between ethyl acetate
dry with materialThe organic phase was dried (MgSO4)
customevaporated

Sources & evidence

ORD record: ord-12d9608331e54438b2df105fc5bd6d6a
Source dataset: uspto-grants-2003_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06579872B1

Reaction notes

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