Propionic Acid → HCID 59141509, compound

HRID 252893Notes

Reaction equation

HRID 252893 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:40])[CH2:28][CH2:29][CH2:30][N:31]([CH2:38][CH3:39])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)=[CH2:25].S(=O)(=O)(O)[NH2:42]>CO.C(O)(=O)C>[CH:24]([O:26][C:27](=[O:40])[CH2:28][CH2:29][CH2:30][N:31]([C:32]1[CH:37]=[CH:36][C:35]([N:42]=[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:34][CH:33]=1)[CH2:38][CH3:39])=[CH2:25]

Participants

8

Reactant 5

HCID 1032Propionic AcidHCID 5987Sulfamic AcidHCID 84922-Chloro-4-nitroanilineHCID 82157Nitrosylsulfuric acidHCID 67267009HCID 67267009, compound

Product 1

HCID 59141509HCID 59141509, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 887MethanolSolvent

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 7.0 parts of 4-(ethyl-phenyl-amino)-butyric 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 10.4 parts of 4-{[4-(2-chloro-4-nitrophenylazo)-phenyl]-ethyl-amino}-butyric acid vinyl ester. λmax=509 nm (DMF).

Workup

  1. customwas held below 10° C
  2. stirringWith stirring
  3. additionthe diazotization mixture was slowly added
  4. stirringThe reaction mixture was stirred over night
  5. customthe product was isolated by filtration
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-c669119f93f449259916480829767a9b
Source dataset
uspto-grants-2011_01
Patent number
US07871446B2

Reaction notes

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