Hydrochloric Acid → HCID 54401129, compound

HRID 1389116Notes

Reaction equation

HRID 1389116 reaction equation
FC1C=C([N+]([O-])=O)C=CC=1C=CC(O)=O.BrBr.Cl.C(O)(=O)C#C.BrCCCCCCCCCCCCCCCC.[F:41][C:42]1[CH:47]=[C:46]([NH:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][CH2:59][CH2:60][CH2:61][CH2:62][CH2:63][CH3:64])[CH:45]=[CH:44][C:43]=1[C:65]#[C:66][C:67]([O:69]CC)=[O:68]>C(O)(=O)C.[OH-].[Na+].[OH-].[NH4+]>[F:41][C:42]1[CH:47]=[C:46]([NH:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][CH2:59][CH2:60][CH2:61][CH2:62][CH2:63][CH3:64])[CH:45]=[CH:44][C:43]=1[C:65]#[C:66][C:67]([OH:69])=[O:68]

Participants

10

Reactant 6

HCID 313Hydrochloric AcidHCID 82131-BromohexadecaneHCID 10110Propiolic AcidHCID 24408BromineHCID 544247862-Fluoro-4-nitrocinnamic acidHCID 54428487Ethyl 2-fluoro-4-(hexadecylamino)phenylpropiolate

Product 1

HCID 54401129HCID 54401129, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 14798Sodium HydroxideSolventHCID 14923Ammonium HydroxideSolvent

Procedure

Alternatively, the 2-fluoro-4-aminophenylpropiolic acid is prepared from 2-fluoro-4-nitrocinnamic acid by successive treatment with bromine in acetic acid, aqueous sodium hydroxide, ferric sulfate and ammonium hydroxide, and ethanolic hydrogen chloride. The propiolic acid is then converted to the corresponding ethyl ester and alkylated with 1-bromohexadecane in the manner of Example 9. The resulting ethyl 2-fluoro-4-(hexadecylamino)phenylpropiolate is hydrolyzed in the manner of Example 10 to yield 2-fluoro-4-(hexadecylamino)phenylpropiolic acid.

Sources & evidence

ORD record
ord-e5478f55a02b4add9afc5b20aaef5120
Source dataset
uspto-grants-1981_01
Patent number
US04243609

Reaction notes

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