Benzene → Methyl 6-aminoquinoline-5-carboxylate

HRID 1725878Notes

Reaction equation

HRID 1725878 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][C:9]2[N:8]=[CH:7][CH:6]=[CH:5][C:4]=2[C:3]=1[C:12]([OH:14])=[O:13].[CH:15]1C=CC=CC=1.[Si](C=[N+]=[N-])(C)(C)C>CO>[NH2:1][C:2]1[CH:11]=[CH:10][C:9]2[N:8]=[CH:7][CH:6]=[CH:5][C:4]=2[C:3]=1[C:12]([O:14][CH3:15])=[O:13]

Participants

5

Reactant 3

HCID 241BenzeneHCID 167693TrimethylsilyldiazomethaneHCID 205642906-Aminoquinoline-5-carboxylic acid

Product 1

HCID 45089602Methyl 6-aminoquinoline-5-carboxylate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of Example 96A (0.43 g, 2.3 mmol), benzene (10 mL), and methanol (4 mL) was treated with TMSCHN2 (2.0 mL, 4.0 mmol, 2.0M solution in hexanes), stirred at room temperature for 90 minutes, quenched with glacial acetic acid, and concentrated. The residue was diluted with ethyl acetate, washed with saturated Na2CO3, dried (MgSO4), filtered, and concentrated to provide the desired product (0.401 g). MS (DCI) m/e 220 (M+NH4)+.

Workup

  1. customquenched with glacial acetic acid
  2. concentrationconcentrated
  3. additionThe residue was diluted with ethyl acetate
  4. washwashed with saturated Na2CO3
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-1e8b4c0439874300b29d7cb572a86c18
Source dataset
uspto-grants-2009_02
Patent number
US07491718B2

Reaction notes

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