Hydrochloric Acid → HCID 136102194, compound

HRID 629814Notes

Reaction equation

HRID 629814 reaction equation
[OH-].[K+].[CH2:3]([C:9]1[C:10]2[NH:14][C:13]([C:15]([C:49]3[CH:54]=[CH:53][C:52]([C:55]([O:57]C)=[O:56])=[CH:51][CH:50]=3)=[C:16]3[N:48]=[C:19]([C:20]([CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH3:47])=[C:21]4[NH:41][C:24](=[C:25]([C:31]5[CH:36]=[CH:35][C:34]([C:37]([O:39]C)=[O:38])=[CH:33][CH:32]=5)[C:26]5[CH:27]=[CH:28][C:29]=1[N:30]=5)[CH:23]=[CH:22]4)[CH:18]=[CH:17]3)=[CH:12][CH:11]=2)[CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].O.Cl>CO.C1COCC1>[C:37]([C:34]1[CH:33]=[CH:32][C:31]([C:25]2[C:24]3[NH:41][C:21]([C:20]([CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH3:47])=[C:19]4[N:48]=[C:16]([C:15]([C:49]5[CH:50]=[CH:51][C:52]([C:55]([OH:57])=[O:56])=[CH:53][CH:54]=5)=[C:13]5[NH:14][C:10](=[C:9]([CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8])[C:29]6[CH:28]=[CH:27][C:26]=2[N:30]=6)[CH:11]=[CH:12]5)[CH:17]=[CH:18]4)=[CH:22][CH:23]=3)=[CH:36][CH:35]=1)([OH:39])=[O:38]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14797Potassium HydroxideHCID 136102203HCID 136102203, compound

Product 1

HCID 136102194HCID 136102194, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

In a typical experiment, a solution of KOH (200 mg, 3.6 mmol) in methanol (1 ml) was added to a stirred solution of 5,15-dihexyl-10,20-bis-(4-methoxycarbonylphenyl)-porphyrin (31 mg, 0.04 mmol) in THF (8 ml) and the reaction mixture was stirred for 2 d. Water (50 ml) and hydrochloric acid were then added until the pH was adjusted to 4-6. The aqueous layer was extracted with dichloromethane (2×100 ml) and the organic layer was separated, washed with water until neutral and dried over sodium sulfate. The solvent was evaporated and the title compound 5,15-bis-(4-carboxyphenyl)-10,20-dihexyl-porphyrin was obtained after recrystallization from dichloromethane/aqueous methanol (26 mg, 87%).

Workup

  1. extractionThe aqueous layer was extracted with dichloromethane (2×100 ml)
  2. customthe organic layer was separated
  3. washwashed with water until neutral and
  4. dry with materialdried over sodium sulfate
  5. customThe solvent was evaporated

Sources & evidence

ORD record
ord-a57b0712541243b3907c13acc18b4350
Source dataset
uspto-grants-2016_04
Patent number
US09315510B2

Reaction notes

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