Sodium Hydroxide → 7-Nitro-3,4-dihydro-2,2-dimethyl-trans-4-(3-carbethoxypropylamino)-2H-benzo[b]pyran-3-ol

HRID 543469Notes

Reaction equation

HRID 543469 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]2[CH:12]3[O:13][CH:11]3[C:10]([CH3:15])([CH3:14])[O:9][C:8]=2[CH:16]=1)([O-:3])=[O:2].Cl.[NH2:18][CH2:19][CH2:20][CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23].[OH-].[Na+]>C(O)C>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]2[C@@H:12]([NH:18][CH2:19][CH2:20][CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23])[C@H:11]([OH:13])[C:10]([CH3:15])([CH3:14])[O:9][C:8]=2[CH:16]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 126496614-Aminobutyrate ethyl hydrochlorideHCID 132229227-Nitro-3,4-dihydro-2,2-dimethyl-3,4-epoxy-2H-benzo[b]pyran

Product 1

HCID 137043357-Nitro-3,4-dihydro-2,2-dimethyl-trans-4-(3-carbethoxypropylamino)-2H-benzo[b]pyran-3-ol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

7-Nitro-3,4-dihydro-2,2-dimethyl-3,4-epoxy-2H-benzo[b]pyran (0.48 g, the preparation of which is described in Example 3 of U.K. Pat. No. 1,548,221), ethyl 4-aminobutyrate hydrochloride (0.34 g) and sodium hydroxide pellets (0.08 g) were refluxed in ethanol (50 ml) for 12 hours. Filtration and evaporation and chromatography on a chromatotron (2 mm silica gel HF254, gradient elution with pentane-ethyl acetate) gave recovered epoxide (0.20 g) and trans-4-(3-carbethoxypropylamino)-7-nitro-2,2-dimethyl-2H-benzo[b]pyran-3-ol (0.21 g) as a gum, which was used as such in Example 10.

Workup

  1. filtrationFiltration and evaporation and chromatography
  2. washon a chromatotron (2 mm silica gel HF254, gradient elution with pentane-ethyl acetate)
  3. customgave
  4. customrecovered epoxide (0.20 g) and trans-4-(3-carbethoxypropylamino)-7-nitro-2,2-dimethyl-2H-benzo[b]pyran-3-ol (0.21 g) as a gum, which

Sources & evidence

ORD record
ord-4c89c0c8e9f344f7897ac927ea1305d5
Source dataset
uspto-grants-1984_05
Patent number
US04446113

Reaction notes

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