Ammonium Hydroxide → 4-(Aminomethylidene)-1-benzoxepine-3,5(2H,4H)-dione

HRID 1730085Notes

Reaction equation

HRID 1730085 reaction equation
[OH-].[NH4+:2].Br[CH2:4][C:5]([C:7]1[C:16](=[O:17])[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[O:9][CH:8]=1)=[O:6]>CO>[NH2:2][CH:8]=[C:7]1[C:16](=[O:17])[C:15]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[O:9][CH2:4][C:5]1=[O:6]

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 214864043-(Bromoacetyl)-4H-1-benzopyran-4-one

Product 1

HCID 542639514-(Aminomethylidene)-1-benzoxepine-3,5(2H,4H)-dione

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Concentrated ammonium hydroxide (1300ml) was added to a stirred mixture of 108g (0.041 mole) of 3(bromoacetyl)chromone and 500ml of methanol. All solid went into solution. There was a mild exotherm. After several minutes the product began to separate. After one hour, the reddish-tan solid was filtered, washed well with water and dried; wt. 70g (86%); m.p. 149°-151°. Recrystallization from ethyl acetate gave pure, orange crystals; m.p. 151°-153°.

Workup

  1. waitAfter several minutes the product began
  2. customto separate
  3. filtrationthe reddish-tan solid was filtered
  4. washwashed well with water
  5. customdried
  6. customRecrystallization from ethyl acetate
  7. customgave pure

Sources & evidence

ORD record
ord-5d91042cc391498db261c74d5c77a095
Source dataset
uspto-grants-1976_11
Patent number
US03991082

Reaction notes

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