HCID 21460173, compound → HCID 21460065, compound

HRID 1941225Notes

Reaction equation

HRID 1941225 reaction equation
[N:1]1([C:7]2[O:8][C:9]3[CH:20]=[CH:19][CH:18]=[CH:17][C:10]=3[C:11](=[O:16])[C:12]=2[N+:13]([O-])=O)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1>CCOC(C)=O.[Pd]>[NH2:13][C:12]1[C:11](=[O:16])[C:10]2[CH:17]=[CH:18][CH:19]=[CH:20][C:9]=2[O:8][C:7]=1[N:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1

Participants

4

Reactant 1

HCID 21460173HCID 21460173, compound

Product 1

HCID 21460065HCID 21460065, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

Part B: 2-(4-Morpholinyl)-3-nitro-4H-1-benzopyran-4-one(500 mg) is dissolved in EtOAc (30 mL). Palladium on carbon (10%, 100 mg) is added under a nitrogen atmosphere. The mixture is fixed to a Parr hydrogenator at 30 psi for 4 hr, then filtered (Celite, 1 cm) and solvent removed in vacuo. The product is purified by flash chromatography (EtOAc) to give 3-Amino-2-(morpholinyl)-4H-1-benzopyran-4-one (419 mg, 94%). Mp 140°-1° C.; IR (mull) 2954, 2925, 2856, 1621, 1607, 1551, 1466, 1423, 1382, 1277, 1271, 1240, 1115, 952, 762 cm-1 ; 1H NMR (CDCl3, δ) 8.24 (dd, J=7.8, 2.0 Hz, 1H), 7.60 (ddd, J=6.8, 6.7, 1.8 Hz, 1 H) , 7.38 (br.d, J=7.8 Hz, 2 H), 3.91-3.76 (m, 4 H), 3.52-3.47 (m, 4 H), 3.43 (br.s, 2 H); UV (EtOH) λ max (ε) 212 (19,150), 233 (15,180), 255sh (9,900), 300 (3,000), 356 (12,100); Mass spectrum:ions at m/e (relative intensity) 262 (21), 246 (100), 201 (21), 188 (18), 187 (40), 148 (88), 121 (52), 114 (21), 70 (36), 42 (17); Anal. calc'd. for C13H14N2O3 : C, 63.40, H, 5.73, N, 11.38; found: C, 63.48; H, 5.84; N, 11.46.

Workup

  1. filtrationfiltered (Celite, 1 cm) and solvent
  2. customremoved in vacuo
  3. customThe product is purified by flash chromatography (EtOAc)

Sources & evidence

ORD record
ord-14e02eb23ce24416bbd480b8a2c94d1d
Source dataset
uspto-grants-1997_12
Patent number
US05703075

Reaction notes

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