Hydrochloric Acid → HCID 136102190, compound

HRID 629815Notes

Reaction equation

HRID 629815 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]([C:38]4[CH:43]=[CH:42][C:41]([C:44]([O:46]C)=[O:45])=[CH:40][CH:39]=4)=[C:21]4[NH:37][C:24](=[C:25]([CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36])[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:44]([C:41]1[CH:42]=[CH:43][C:38]([C:20]2[C:21]3[NH:37][C:24]([C:25]([CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36])=[C:26]4[N:30]=[C:29]([C:9]([CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8])=[C:10]5[NH:14][C:13](=[C:15]([C:49]6[CH:50]=[CH:51][C:52]([C:55]([OH:57])=[O:56])=[CH:53][CH:54]=6)[C:16]6[CH:17]=[CH:18][C:19]=2[N:48]=6)[CH:12]=[CH:11]5)[CH:28]=[CH:27]4)=[CH:23][CH:22]=3)=[CH:39][CH:40]=1)([OH:46])=[O:45]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14797Potassium HydroxideHCID 136102189HCID 136102189, compound

Product 1

HCID 136102190HCID 136102190, 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 5,10-dihexyl-15,20-bis-(4-methoxycarbonylphenyl)-porphyrin (34 mg, 0.05 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 5,10-bis-(4-carboxyphenyl)-15,20-dihexyl-porphyrin was obtained after recrystallization from dichloromethane/aqueous methanol (26 mg, 79%).

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-8a08cd804bcb45349b9fb0e79028071d
Source dataset
uspto-grants-2016_04
Patent number
US09315510B2

Reaction notes

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