Sodium Bicarbonate → HCID 178433820, compound

HRID 384420Notes

Reaction equation

HRID 384420 reaction equation
[NH2:1][C:2]1[C:3]([OH:16])=[C:4]([C:8]2[CH:9]=[C:10]([C:13]([OH:15])=[O:14])[NH:11][CH:12]=2)[CH:5]=[CH:6][CH:7]=1.[N:17]([O-])=O.[Na+].[CH3:21][C:22]1[CH2:23][C:24](=[O:37])[N:25]([C:27]2[CH:36]=[CH:35][C:34]3[CH2:33][CH2:32][CH2:31][CH2:30][C:29]=3[CH:28]=2)[N:26]=1.C(=O)(O)[O-].[Na+]>Cl>[OH:16][C:3]1[C:2]([NH:1][N:17]=[C:23]2[C:24](=[O:37])[N:25]([C:27]3[CH:36]=[CH:35][C:34]4[CH2:33][CH2:32][CH2:31][CH2:30][C:29]=4[CH:28]=3)[N:26]=[C:22]2[CH3:21])=[CH:7][CH:6]=[CH:5][C:4]=1[C:8]1[CH:9]=[C:10]([C:13]([OH:15])=[O:14])[NH:11][CH:12]=1

Participants

6

Reactant 4

HCID 516892Sodium BicarbonateHCID 23668193Sodium NitriteHCID 510365803-Methyl-1-(5,6,7,8-tetrahydronaphthalen-2-yl)-1H-pyrazol-5(4H)-oneHCID 596156694-(3-amino-2-hydroxy-phenyl)-1H-pyrrole-2-carboxylic acid

Product 1

HCID 178433820HCID 178433820, compoundYield 27.7%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

4-(3-Amino-2-hydroxy-phenyl)-1H-pyrrole-2-carboxylic acid 57i (130 mg, 0.43 mmol) was dissolved in hydrochloric acid (1.5 mL, 1 mol/L) upon cooling by an ice-water bath, followed by dropwise addition of 0.6 mL of aqueous sodium nitrite (33 mg, 0.47 mmol). After the mixture was reacted for 10 minutes, 5-methyl-2-(5,6,7,8-tetrahydro-naphthalen-2-yl)-2,4-dihydro-pyrazol-3-one 3i (89 mg, 0.3 mmol) was added. The mixture was adjusted to pH 8˜9 with saturated aqueous sodium bicarbonate. The reaction mixture was reacted at room temperature for 24 hours. The reaction was monitored by TLC until the disappearance of the starting materials. The mixture was filtered and the filter cake was dissolved in 15 mL of water. The mixture was adjusted to pH 3˜4 with concentrated hydrochloric acid upon cooling by an ice-water bath. The mixture was filtered and the filter cake was washed with ethyl acetate and dried to obtain the title compound 4-(2-hydroxy-3-{N′-[3-methyl-5-oxo-1-(5,6,7,8-tetrahydro-naphthalen-2-yl)-1,5-dihydro-pyrazol-4-ylidene]-hydrazino}-phenyl)-1H-pyrrole-2-carboxylic acid 57 (38 mg, yield 21.3%) as a grey solid.

Workup

  1. temperatureupon cooling by an ice-water bath
  2. customAfter the mixture was reacted for 10 minutes
  3. customThe reaction mixture was reacted at room temperature for 24 hours
  4. filtrationThe mixture was filtered
  5. dissolutionthe filter cake was dissolved in 15 mL of water
  6. temperatureupon cooling by an ice-water bath
  7. filtrationThe mixture was filtered
  8. washthe filter cake was washed with ethyl acetate
  9. customdried

Sources & evidence

ORD record
ord-1420ab80a5be465686801675b7d11cb1
Source dataset
uspto-grants-2013_02
Patent number
US08367710B2

Reaction notes

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