Hydrochloric Acid → HCID 10542456, compound

HRID 1107637Notes

Reaction equation

HRID 1107637 reaction equation
[CH2:1]([O:8][C:9]1[C:18]2[C:13](=[CH:14][C:15]([C:19]#[N:20])=[CH:16][CH:17]=2)[CH:12]=[C:11]([C:21]([O:23]CC)=[O:22])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.CCO.[K+].[Br-]>C1COCC1.CO.O>[CH2:1]([O:8][C:9]1[C:18]2[C:13](=[CH:14][C:15]([C:19]#[N:20])=[CH:16][CH:17]=2)[CH:12]=[C:11]([C:21]([OH:23])=[O:22])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 253877Potassium BromideHCID 10664234HCID 10664234, compound

Product 1

HCID 10542456HCID 10542456, compound

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Conditions

Temperature
25 °C

Procedure

A solution of 13 (8.67 g, 26.2 mmol) in 260 mL of THF--CH3OH--H2O (3:1:1) was treated with LiOH--H2O (5.49 g, 131 mmol, 5 equiv) and the mixture was stirred at 25° C. for 25 h. The solution was acidified with the addition of 10% aqueous HCl (pH<1) and the product partially precipitated. The product was collected by filtration and the remaining aqueous phase was extracted with EtOAc (3×200 mL). The combined organic layers were dried (MgSO4) and concentrated in vacuo to afford a combined 14 (7.94 g, 7.94 g theoretical, 100%): mp 235° C. (white powder, EtOH); 1H NMR (DMSO-d6, 400 MHz) δ8.73 (d, 1H, J=1.1 Hz), 8.34 (d, 1H, J=8.9 Hz), 8.32 (s, 1H), 7.88 (dd, 1H, J=1.5, 8.9 Hz), 7.63 (s, 1H), 7.57-7.34 (m, 5H), 5.38 (s, 2H); 13C NMR (CDCl3, 100 MHz) δ167.3, 153.8, 136.6, 135.5, 132.3, 130.3, 128.6, 128.3, 128.1, 127.6, 126.4, 123.4, 121.9, 118.8, 110.0, 107.5, 70.0; IR (KBr) vmax 3000 (br), 2227, 1687, 1577, 1499, 1419, 1343, 1283, 1250, 1105, 996, 915, 836, 740 cm-1 ; FABHRMS (NBA) m/z 304.0964 (M+ +H, C19H13NO3 requires 304.0974).

Workup

  1. customthe product partially precipitated
  2. filtrationThe product was collected by filtration
  3. extractionthe remaining aqueous phase was extracted with EtOAc (3×200 mL)
  4. dry with materialThe combined organic layers were dried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customto afford a combined 14 (7.94 g, 7.94 g theoretical, 100%)

Sources & evidence

ORD record
ord-15c02525e2c642aaab80e4c9a9b40a29
Source dataset
uspto-grants-2000_05
Patent number
US06060608

Reaction notes

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