Propionic Acid → 3-{[4-(2-Chloro-4-nitrophenylazo)-phenyl]-ethyl-amino}-propionic acid vinyl ester

HRID 252889

Reaction equation

[Cl:1][C:2]1[CH:8]=[C:7]([N+:9]([O-:11])=[O:10])[CH:6]=[CH:5][C:3]=1[NH2:4].C(O)(=O)CC.N(OS(=O)(=O)O)=O.[CH:24]([O:26][C:27](=[O:39])[CH2:28][CH2:29][N:30]([CH2:37][CH3:38])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)=[CH2:25].S(=O)(=O)(O)[NH2:41]>CO.C(O)(=O)C>[CH:24]([O:26][C:27](=[O:39])[CH2:28][CH2:29][N:30]([C:31]1[CH:36]=[CH:35][C:34]([N:41]=[N:4][C:3]2[CH:5]=[CH:6][C:7]([N+:9]([O-:11])=[O:10])=[CH:8][C:2]=2[Cl:1])=[CH:33][CH:32]=1)[CH2:37][CH3:38])=[CH2:25]

Participants

Conditions

Temperature: 5 °C

Procedure

5.2 parts of 2-chloro-4-nitroaniline, 20 parts of propionic acid and 30 parts of acetic acid were charged and cooled to 5° C. 11.4 parts of 40% (w/w) nitrosyl sulfuric acid were added, whilst the temperature was held below 10° C. The diazotization mixture was stirred for a further 2 hrs at 5-10° C. To a separate vessel were charged 6.5 parts of 3-(ethyl-phenyl-amino)-propionic acid vinyl ester, 100 parts of methanol, 1 part sulfamic acid and 100 parts of ice. With stirring, the diazotization mixture was slowly added followed by a further 300 parts of ice. The reaction mixture was stirred over night and the product was isolated by filtration, washed with water and dried to yield 9.9 parts of 3-{[4-(2-chloro-4-nitrophenylazo)-phenyl]-ethyl-amino}-propionic acid vinyl ester. λmax=510 nm (DMF).

Workup

customwas held below 10° C
stirringWith stirring
additionthe diazotization mixture was slowly added
stirringThe reaction mixture was stirred over night
customthe product was isolated by filtration
washwashed with water
customdried

Sources & evidence

ORD record: ord-8cd0f8752a0d4b329b490afb81d525b9
Source dataset: uspto-grants-2011_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07871446B2

Linked notes

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