Hydrochloric Acid → HCID 178493302, compound

HRID 551602Notes

Reaction equation

HRID 551602 reaction equation
C([NH:4][CH2:5][CH2:6][C:7]1[CH:8]=[CH:9][C:10]([O:36][CH3:37])=[C:11]([NH:13][C:14](=[O:35])[C:15](=[N:19][NH:20][C:21]2[CH:26]=[CH:25][C:24]([N+:27]([O-:29])=[O:28])=[C:23]([N+]([O-])=O)[C:22]=2[O:33][CH3:34])[C:16](=[O:18])[CH3:17])[CH:12]=1)(=O)C.CN1C(=O)CCC1.Cl>O>[NH2:4][CH2:5][CH2:6][C:7]1[CH:8]=[CH:9][C:10]([O:36][CH3:37])=[C:11]([NH:13][C:14](=[O:35])[C:15](=[N:19][NH:20][C:21]2[CH:26]=[CH:25][C:24]([N+:27]([O-:29])=[O:28])=[CH:23][C:22]=2[O:33][CH3:34])[C:16](=[O:18])[CH3:17])[CH:12]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 13387N-methyl-2-pyrrolidoneHCID 178490319HCID 178490319, compound

Product 1

HCID 178493302HCID 178493302, compoundYield 104.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
112 °C

Procedure

The product described in the previous step, N-[5-(2-acetamidoethyl)-2-methoxyphenyl]-2-[(2-methoxy-4-nitronitrophenyl)-hydrazono]-3-oxobutyramide (4.6 g) was mixed with 150 mL of NMP and 20 mL of concentrated HCl and heated at 112° C. for 6 hours. The reaction mixture was poured into 1000 mL of water and left overnight. The resulting precipitate was filtered off, washed with water and then with a dilute aqueous NaHCO3 solution to a neutral pH, and finally dried in a vacuum to give 4.0 g (95.2%) of N-[5-(2-aminoethyl)-2-methoxyphenyl]-2-[(2-methoxy-4-nitro-phenyl)-hydrazono]-3-oxo-butyramide (AePY74) as a yellow powder. 1HNMR (DMSO-d6) spectrum was consistent with the desired product.

Workup

  1. filtrationThe resulting precipitate was filtered off
  2. washwashed with water
  3. dry with materialwith a dilute aqueous NaHCO3 solution to a neutral pH, and finally dried in a vacuum

Sources & evidence

ORD record
ord-dadd8183a25347c48db0b56984503753
Source dataset
uspto-grants-2011_05
Patent number
US07947761B2

Reaction notes

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