Dimethylformamide → HCID 178490963, compound

HRID 1640122Notes

Reaction equation

HRID 1640122 reaction equation
[CH3:1][O:2][C:3]1[CH:20]=[CH:19][C:6]([CH2:7][NH:8][C:9]2[N+:10]([O-:18])=[CH:11][CH:12]=[C:13]([N+]([O-])=O)[CH:14]=2)=[CH:5][CH:4]=1.[OH:21][C:22]1[CH:31]=[C:30]2[C:25]([CH2:26][CH2:27][CH:28]([C:32]([OH:34])=[O:33])[CH2:29]2)=[CH:24][CH:23]=1.C(=O)([O-])[O-].[Cs+].[Cs+].CN(C=O)C>>[CH3:1][O:2][C:3]1[CH:20]=[CH:19][C:6]([CH2:7][NH:8][C:9]2[CH:14]=[C:13]([O:21][C:22]3[CH:31]=[C:30]4[C:25]([CH2:26][CH2:27][CH:28]([C:32]([OH:34])=[O:33])[CH2:29]4)=[CH:24][CH:23]=3)[CH:12]=[CH:11][N+:10]=2[O-:18])=[CH:5][CH:4]=1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 10796Cesium carbonateHCID 145412687-Hydroxy-1,2,3,4-tetrahydronaphthalene-2-carboxylic acidHCID 178490962HCID 178490962, compound

Product 1

HCID 178490963HCID 178490963, compoundYield 89.2%

Conditions

Temperature
80 °C

Procedure

A mixture of N-(4-methoxybenzyl)-4-nitropyridin-2-amine 1-oxide (25.6 g, 0.0929 mol), 7-hydroxy-1,2,3,4-tetrahydronaphthalene-2-carboxylic acid (17 g, 0.088 mol) and cesium carbonate (92 g, 0.28 mol) in DMF (200 mL, 3 mol) was heated with stirring at 80° C. overnight. The reaction mixture was allowed to cool and then concentrated to small volume and 200 ml of water was added. The solution was acidified with conc. HCl to pH=4. The aqueous solution was removed and the remaining organic solution was washed with water (3×). The residue was treated with 1N NaOH (150 ml) and extracted with DCM (3×). The aqueous solution was acidified with conc. HCl. A precipitate formed and was filtered, washed with water (3×), and dried to give 7-({2-[(4-methoxybenzyl)amino]-1-oxidopyridin-4-yl}oxy)-1,2,3,4-tetrahydronaphthalene-2-carboxylic acid (33 g, 89%) as a brown solid. 1H NMR (d6-DMSO, 400 MHz) δ: 12.40 (s, 1H); 8.03 (d, 1H); 7.80 (t, 1H); 7.20 (d, 2H); 7.12 (d, 1H); 6.82 (d, 2H); 6.76 (m, 2H); 6.20 (s, 1H); 6.10 (d, 1H); 4.30 (d, 1H); 3.70 (s, 3H); 2.80 (m, 4H); 2.65 (m, 1H); 2.08 (m, 1H); 1.74 (m, 1H) LCMS ES+ 421.1

Workup

  1. temperaturewas heated
  2. temperatureto cool
  3. concentrationconcentrated to small volume and 200 ml of water
  4. additionwas added
  5. customThe aqueous solution was removed
  6. washthe remaining organic solution was washed with water (3×)
  7. additionThe residue was treated with 1N NaOH (150 ml)
  8. extractionextracted with DCM (3×)
  9. customA precipitate formed
  10. filtrationwas filtered
  11. washwashed with water (3×)
  12. customdried

Sources & evidence

ORD record
ord-cd6f9931e1e54277b662a529364e685c
Source dataset
uspto-grants-2012_02
Patent number
US08110687B2

Reaction notes

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