Ammonia → 6-acetamido-trans-4-amino-3,4-dihydro-2,2-dimethyl-7-nitro-2H-benzo[b]pyran-3-ol

HRID 236419Notes

Reaction equation

HRID 236419 reaction equation
[C:1]([NH:4][C:5]1[C:17]([N+:18]([O-:20])=[O:19])=[CH:16][C:8]2[O:9][C:10]([CH3:15])([CH3:14])[CH:11]3[O:13][CH:12]3[C:7]=2[CH:6]=1)(=[O:3])[CH3:2].[NH3:21]>C(O)C>[C:1]([NH:4][C:5]1[C:17]([N+:18]([O-:20])=[O:19])=[CH:16][C:8]2[O:9][C:10]([CH3:15])([CH3:14])[C@@H:11]([OH:13])[C@H:12]([NH2:21])[C:7]=2[CH:6]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 110657616-Acetamido-3,4-epoxy-3,4-dihydro-2,2-dimethyl-7-nitro-2H-benzo[b]pyran

Product 1

HCID 137043376-acetamido-trans-4-amino-3,4-dihydro-2,2-dimethyl-7-nitro-2H-benzo[b]pyran-3-ol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

6-Acetamido-3,4-epoxy-3,4-dihydro-2,2-dimethyl-7-nitro-2H-benzo[b]pyran (1.0 g, the preparation of which is described in European Pat. No. 28,064) was dissolved in dry ethanol (150 ml) and saturated with ammonia during 3 h, with cooling. The reaction mixture was stirred at room temperature for 5 days and evaporated. The crude residue was purified on the chromatotron (80% ethyl acetate-pentane to 20% methanol-ethyl acetate gradient elution), to give the title compound (410 mgm). A small portion was converted to the hydrochloride salt and recrystallised from ethanol-diethyl ether, with m.p. 258°-261° C.

Workup

  1. temperaturewith cooling
  2. customevaporated
  3. customThe crude residue was purified on the chromatotron (80% ethyl acetate-pentane to 20% methanol-ethyl acetate gradient elution)

Sources & evidence

ORD record
ord-d5e8e61e6edd461fbc7daab6be13d172
Source dataset
uspto-grants-1987_02
Patent number
US04644070

Reaction notes

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