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Hydrochloric Acid → HCID 86676736, compound

HRID 573399
Notes
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Reaction equation

HRID 573399 reaction equation
[NH2:1][C:2]1[C:11]([N+:12]([O-])=O)=[C:10]2[C:5]([C:6](=[O:24])[CH:7]=[C:8]([C:15]3[CH:20]=[CH:19][C:18]([N:21]([CH3:23])[CH3:22])=[CH:17][CH:16]=3)[O:9]2)=[CH:4][CH:3]=1.[H][H].[ClH:27]>CO.[Pd]>[ClH:27].[NH2:1][C:2]1[C:11]([NH2:12])=[C:10]2[C:5]([C:6](=[O:24])[CH:7]=[C:8]([C:15]3[CH:20]=[CH:19][C:18]([N:21]([CH3:22])[CH3:23])=[CH:17][CH:16]=3)[O:9]2)=[CH:4][CH:3]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 665216767-Amino-2-(4-(dimethylamino)phenyl)-8-nitro-4H-chromen-4-oneHCID 178418361HCID 178418361, compound

Product 1

HCID 86676736HCID 86676736, compoundYield 88%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst
HCID 887
Methanol
Solvent

Procedure

A solution of 7-amino-2-(4-(dimethylamino)phenyl)-8-nitro-4H-chromen-4-one (4, 900 mg, 2.77 mmol) and 10% Pd/C (450 mg) in methanol (9 mL) and concentrated hydrochloride (aq., 9 mL) was stirred at the atmosphere of hydrogen overnight. The solid was filtered and the filtrate was evaporated in reduced pressure to afford 7,8-diamino-2-(4-(dimethylamino)phenyl)-4H-chromen-4-one hydrochloride (5) as a light yellow solid (810 mg, yield: 88%).

Workup

  1. filtrationThe solid was filtered
  2. customthe filtrate was evaporated in reduced pressure

Sources & evidence

ORD record
ord-2a8acfe5277a4cf89922e6f4dd1ee14f
Source dataset
uspto-grants-2015_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09029561B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes