Sodium Bicarbonate → HCID 178433821, compound

HRID 238722Notes

Reaction equation

HRID 238722 reaction equation
Br.[NH2:2][C:3]1[C:4]([OH:17])=[C:5]([C:9]2[CH:10]=[C:11]([C:14]([OH:16])=[O:15])[O:12][CH:13]=2)[CH:6]=[CH:7][CH:8]=1.[N:18]([O-])=O.[Na+].[CH3:22][C:23]1[CH2:24][C:25](=[O:38])[N:26]([C:28]2[CH:37]=[CH:36][C:35]3[CH2:34][CH2:33][CH2:32][CH2:31][C:30]=3[CH:29]=2)[N:27]=1.C(=O)(O)[O-].[Na+]>Cl.C(O)C>[OH:17][C:4]1[C:3]([NH:2]/[N:18]=[C:24]2/[C:23]([CH3:22])=[N:27][N:26]([C:28]3[CH:37]=[CH:36][C:35]4[CH2:34][CH2:33][CH2:32][CH2:31][C:30]=4[CH:29]=3)[C:25]/2=[O:38])=[CH:8][CH:7]=[CH:6][C:5]=1[C:9]1[CH:10]=[C:11]([C:14]([OH:16])=[O:15])[O:12][CH:13]=1

Participants

7

Reactant 4

HCID 516892Sodium BicarbonateHCID 23668193Sodium NitriteHCID 510365803-Methyl-1-(5,6,7,8-tetrahydronaphthalen-2-yl)-1H-pyrazol-5(4H)-oneHCID 574838264-(3-Amino-2-hydroxy-phenyl)-furan-2-carboxylic acid hydrobromide

Product 1

HCID 178433821HCID 178433821, compoundYield 5.6%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolvent

Procedure

4-(3-Amino-2-hydroxy-phenyl)-furan-2-carboxylic acid 22e (170 mg, 0.57 mmol) was dissolved in hydrochloric acid (1.9 mL, 1 M) upon cooling by an ice-water bath, followed by dropwise addition of 0.7 mL of sodium nitrite solution (43 mg, 0.63 mmol). After the mixture was reacted for 20 minutes, 5-methyl-2-(5,6,7,8-tetrahydro-naphthalen-2-yl)-2,4-dihydro-pyrazol-3-one 7c (116 mg, 0.51 mmol) was added. The mixture was adjusted to pH 8-9 with saturated sodium bicarbonate solution followed by addition of 2 mL of ethanol. The mixture was reacted at room temperature for 24 hours. The mixture was filtered and then 15 mL of water was added to the filter cake. Upon cooling by an ice-water bath, the mixture was adjusted to pH 2-3 with concentrated hydrochloric acid and filtered. The filter cake was washed with ethyl acetate and dried to obtain the title compound (Z)-4-(2-hydroxy-3-{N′-[3-methyl-5-oxo-1-(5,6,7,8-tetrahydro-naphthal-2-yl)-1,5-dihydro-pyrazol-4-ylidene]-hydrazino}-phenyl)-furan-2-carboxylic acid 22f (13 mg, yield 5.5%) as a red solid.

Workup

  1. temperatureupon cooling by an ice-water bath
  2. customAfter the mixture was reacted for 20 minutes
  3. customThe mixture was reacted at room temperature for 24 hours
  4. filtrationThe mixture was filtered
  5. addition15 mL of water was added to the filter cake
  6. temperatureUpon cooling by an ice-water bath
  7. filtrationfiltered
  8. washThe filter cake was washed with ethyl acetate
  9. customdried

Sources & evidence

ORD record
ord-2861e4f451824c288a4d44035176fe5a
Source dataset
uspto-grants-2014_02
Patent number
US08642637B2

Reaction notes

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