4-Morpholino-2-naphthol → 4-Morpholino-2-naphthol

HRID 54603Notes

Reaction equation

HRID 54603 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[CH:10]=[C:9]([OH:17])[CH:8]=2)[CH2:3][CH2:2]1.[CH2:18]([C:27]([CH2:31][C:32]1[CH:37]=[CH:36][C:35]([O:38][CH3:39])=[CH:34][CH:33]=1)([OH:30])[C:28]#[CH:29])[C:19]1[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=1>C1(C)C=CC=CC=1>[O:1]1[CH2:2][CH2:3][N:4]([C:7]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[CH:10]=[C:9]([OH:17])[CH:8]=2)[CH2:5][CH2:6]1.[CH2:18]([C:27]1([CH2:31][C:32]2[CH:37]=[CH:36][C:35]([O:38][CH3:39])=[CH:34][CH:33]=2)[O:30][C:9]2[CH:8]=[C:7]([N:4]3[CH2:3][CH2:2][O:1][CH2:6][CH2:5]3)[C:16]3[C:11]([C:10]=2[CH:29]=[CH:28]1)=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:19]1[CH:20]=[CH:21][C:22]([O:25][CH3:26])=[CH:23][CH:24]=1

Participants

5

Reactant 2

HCID 109880424-Morpholino-2-naphtholHCID 570825081,1-Dianisylprop-2-yn-1-ol

Product 2

HCID 109880424-Morpholino-2-naphtholHCID 70342857HCID 70342857, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

4-Morpholino-2-naphthol was prepared as described in Example 2(b). A mixture of 4-morpholino-2-naphthol (0.50 g;0.0022 mol), 1,1-dianisylprop-2-yn-1-ol (0.59 g; 0.0022 mol), acidic alumina Brockmann 1(4 g) and toluene (35.0 ml) was heated and stirred for 1.5 h, cooled, filtered and the solid washed with toluene. The filtrate was evaporated to give an orange crystalline solid which was washed with diethyl ether to give 3,3-dianisyl -6-morpholino-3H-naphtho[2,1-b]pyran as a white solid (0.61 g;58% yield), m.pt. 211°-213° C. ##STR21##

Workup

  1. temperaturewas heated
  2. temperaturecooled
  3. filtrationfiltered
  4. washthe solid washed with toluene
  5. customThe filtrate was evaporated
  6. customto give an orange crystalline solid which
  7. washwas washed with diethyl ether

Sources & evidence

ORD record
ord-5c7584057b2743f0a680a086a1e315a8
Source dataset
uspto-grants-1997_04
Patent number
US05623005

Reaction notes

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