Hydrochloric Acid → HCID 178479098, compound

HRID 913355Notes

Reaction equation

HRID 913355 reaction equation
[CH2:1]([O:8][C:9]1(O)[CH:18]=[C:17]2[C:12]([CH:13]=[C:14]([N+:19]([O-])=O)[CH:15]=[N:16]2)=[CH:11][CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[ClH:23].CN(C)C=[O:27]>[Pt]>[ClH:23].[NH2:19][C:14]1[CH:15]=[N:16][C:17]2[C:12]([C:13]=1[OH:27])=[CH:11][CH:10]=[C:9]([O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[CH:18]=2

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 67392674HCID 67392674, compound

Product 1

HCID 178479098HCID 178479098, compound

Reagents, catalysts & solvents 1

HCID 23939PlatinumCatalyst

Procedure

A 1 L glass Parr bottle was charged with 7-benzyloxy-3-nitroquinolin-7-ol, anhydrous N,N-dimethylformamide (DMF, 500 mL) and 5% Pt/C catalyst (5.0 g). The vessel was placed on Parr apparatus, evacuated and charged with hydrogen gas (˜45 psi, 3.1×105 Pa). The reaction mixture was shaken overnight. The reaction mixture was filtered through glass fiber filters to remove catalyst. To the resulting dark colored solution was added concentrated hydrochloric acid (12 N HCl, 14 ml, 168.8 mmol). The product precipitated as the hydrochloride salt. The reaction mixture was stirred over the weekend. A solid was collected by vacuum filtration, washed with diethyl ether (100 mL), and air dried overnight to provide 44 g of 3-amino-7-benzyloxyquinolin-4-ol hydrochloride. This material was carried on without further purification.

Workup

  1. customevacuated
  2. additioncharged with hydrogen gas (˜45 psi, 3.1×105 Pa)
  3. filtrationThe reaction mixture was filtered through glass fiber filters
  4. customto remove catalyst
  5. customThe product precipitated as the hydrochloride salt
  6. stirringThe reaction mixture was stirred over the weekend
  7. filtrationA solid was collected by vacuum filtration
  8. washwashed with diethyl ether (100 mL), and air
  9. customdried overnight

Sources & evidence

ORD record
ord-8635665fc404477c9d70cb99bbe92f77
Source dataset
uspto-grants-2011_09
Patent number
US08026366B2

Reaction notes

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