Benzylamine → HCID 12041751, compound

HRID 1263622Notes

Reaction equation

HRID 1263622 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[O:7][C:8]2[C:13]([C:14](=[O:16])[CH:15]=1)=[CH:12][CH:11]=[C:10](OS(C1C=CC(C)=CC=1)(=O)=O)[C:9]=2[N+:28]([O-:30])=[O:29])=[O:5])[CH3:2].[CH2:31]([NH2:38])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1>ClC1C=CC=CC=1Cl.C(OCC)(=O)C>[CH2:1]([O:3][C:4]([C:6]1[O:7][C:8]2[C:13]([C:14](=[O:16])[CH:15]=1)=[CH:12][CH:11]=[C:10]([NH:38][CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[C:9]=2[N+:28]([O-:30])=[O:29])=[O:5])[CH3:2]

Participants

5

Reactant 2

HCID 7504BenzylamineHCID 12041750HCID 12041750, compound

Product 1

HCID 12041751HCID 12041751, compoundYield 67%

Reagents, catalysts & solvents 2

HCID 72391,2-DichlorobenzeneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
170 °C

Procedure

To a solution of 8-nitro-4-oxo-7-(toluene-4-sulfonyloxy)-4H-chromene-2-carboxylic acid ethyl ester (433 mg, 1 mmol) in o-dichlorobenzene was added benzylamine (214 mg, 2 mmol). The reaction mixture was heated at 170° C. for 1 hour, and the solvent was removed in vacuo to give a residue. The residue was dissolved in ethyl acetate and washed sequentially with aqueous HCl (2N 50 ml), NaOH (2N, 50 mL) and water, dried over anhydrous Na2SO4, and filtered. The solvent was evaporated in vacuo to give a solid residue. Recrystallization of the residue from ethyl acetate-hexane (2:1) provided 246 mg (67%) of the title compound: mp 168° C.; 1H NMR (400 MHz, CDCl3): 1.43 (t, J=7 Hz, 3H), 4.45 (q, J =7.0 Hz, 2H), 4.61 (d, J=5.0 Hz, 2H), 6.90 (d, J=9.2 Hz), 7.09 (s, 1H), 7.42-7.32 (m, 5H), 8.04 (t, J=5 Hz, 1H), 8.10 (d, J=9.2 Hz, 1H); IR: 3350, 2980, 1730,1660, 1600,1420,1250 cm−1; MS 369 [M+H]+.

Workup

  1. customthe solvent was removed in vacuo
  2. customto give a residue
  3. washwashed sequentially with aqueous HCl (2N 50 ml), NaOH (2N, 50 mL) and water
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationfiltered
  6. customThe solvent was evaporated in vacuo
  7. customto give a solid residue
  8. customRecrystallization of the residue from ethyl acetate-hexane (2:1)

Sources & evidence

ORD record
ord-0e873758845848a2a9ec28030b34b188
Source dataset
uspto-grants-2003_04
Patent number
US06541501B2

Reaction notes

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