4-Aminobenzoic Acid → HCID 11227079, compound

HRID 1644564Notes

Reaction equation

HRID 1644564 reaction equation
[Cl-].[CH2:2]([N+:4]1[C:9](/[CH:10]=[CH:11]/[C:12]2[CH:17]=[CH:16][C:15]([N:18]3[CH2:22][CH2:21][CH2:20][CH2:19]3)=[CH:14][CH:13]=2)=[CH:8][CH:7]=[CH:6][C:5]=1/[CH:23]=[CH:24]/[C:25]1[CH:30]=[CH:29][C:28]([N:31]2[CH2:35][CH2:34][CH2:33][CH2:32]2)=[CH:27][CH:26]=1)[CH3:3].[Na].[NH2:37][C:38]1[CH:46]=[CH:45][C:41]([C:42]([OH:44])=[O:43])=[CH:40][CH:39]=1>CO>[NH2:37][C:38]1[CH:46]=[CH:45][C:41]([C:42]([O-:44])=[O:43])=[CH:40][CH:39]=1.[CH2:2]([N+:4]1[C:9](/[CH:10]=[CH:11]/[C:12]2[CH:13]=[CH:14][C:15]([N:18]3[CH2:22][CH2:21][CH2:20][CH2:19]3)=[CH:16][CH:17]=2)=[CH:8][CH:7]=[CH:6][C:5]=1/[CH:23]=[CH:24]/[C:25]1[CH:30]=[CH:29][C:28]([N:31]2[CH2:32][CH2:33][CH2:34][CH2:35]2)=[CH:27][CH:26]=1)[CH3:3]

Participants

5

Reactant 3

HCID 9784-Aminobenzoic AcidHCID 5360545SodiumHCID 9805420HCID 9805420, compound

Product 1

HCID 11227079HCID 11227079, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A total of 52.8 g (0.12 mole) of 1-ethyl-(E,E)-2,6-bis[2-[4-(pyrrolidinyl)phenyl]ethenyl]pyridinium chloride and 18.6 grams (0.12 mole) of the sodium salt of 4-aminobenzoic acid (sodium salt of p-aminobenzoic acid, Na+ PABA−) were dissolved in 1.3 liters of methanol and this mixture was allowed to stir at room temperature for 4 days during which time a precipitate formed. The reaction mixture was then filtered and the solid salt was air dried and vacuum dried to yield a first crop of 28.0 grams of 1-ethyl-(E,E)-2,6-bis[2-[4-(pyrrolidinyl)phenyl]ethenyl]pyridinium 4-aminobenzoate salt (also termed the PABA salt). The filtrate was concentrated under vacuum to produce more precipitate. Isolation of the second crop was effected by filtration followed by air drying and vacuum drying of the solid to afford a second crop of 42.6 grams of 1-ethyl-(E,E)-2,6-bis[2-[4-(pyrrolidinyl)phenyl]ethenyl]pyridinium 4-aminobenzoate salt (also termed the PABA salt)—high performance liquid chromatography area per cent (HPLC A %) first crop=99.6% excluding PABA; HPLC A % second crop=99.9% excluding PABA; 1H NMR and Mass Spectral analyses for both crops were consistent with structure of the desired material 1-ethyl-(E,E)-2,6-bis[2-[4-(pyrrolidinyl)phenyl]ethenyl]pyridinium 4-aminobenzoate salt. This product is also named 1-ethyl-(E,E)-2,6-bis[2-[4-(pyrrolidinyl)phenyl]ethenyl]pyridinium p-aminobenzoate salt or 1-ethyl-(E,E)-2,6-bis[2-[4-(pyrrolidinyl)phenyl]ethenyl]pyridinium PABA salt.

Workup

  1. customformed
  2. filtrationThe reaction mixture was then filtered
  3. customdried
  4. customvacuum dried

Sources & evidence

ORD record
ord-3fe3e14699b24a37a70c2cb76b52f294
Source dataset
uspto-grants-2012_02
Patent number
US08124626B2

Reaction notes

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