Sodium Carbonate → HCID 18972535, compound

HRID 2395122Notes

Reaction equation

HRID 2395122 reaction equation
O.NN.[CH3:4][O:5][C:6]1[CH:7]=[CH:8][C:9]2[N:14]([CH3:15])[C:13]3[CH:16]=[CH:17][C:18]([O:32][CH3:33])=[C:19]([CH2:20][N:21]4C(=O)C5C(=CC=CC=5)C4=O)[C:12]=3[O:11][C:10]=2[C:34]=1[CH2:35][C:36]#[N:37].C(=O)([O-])[O-].[Na+].[Na+]>C(Cl)Cl>[NH2:21][CH2:20][C:19]1[C:12]2[O:11][C:10]3[C:34]([CH2:35][C:36]#[N:37])=[C:6]([O:5][CH3:4])[CH:7]=[CH:8][C:9]=3[N:14]([CH3:15])[C:13]=2[CH:16]=[CH:17][C:18]=1[O:32][CH3:33]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 24654Hydrazine hydrate (1:1)HCID 70078412HCID 70078412, compound

Product 1

HCID 18972535HCID 18972535, compoundYield 90.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2.0 ml of ethanolic hydrazine hydrate solution (1M) were added at room temperature to a suspension of 280 mg of [3,7-dimethoxy-6-(1,3-dioxo-2,3-dihydro-1H-isoindol-2-ylmethyl)-10-methyl-10H-dibenz[b,e][1,4]-oxazin-4-yl]-acetonitrile. The reaction mixture was heated to 85° for 4 hours, the cooled and poured into methylene chloride and 10% sodium carbonate solution. The aqueous phase was extracted with ethylene chloride and the combined organic fractions were dried over magnesium chloride and concentrated. The residue was dried in a high vacuum and, after recrystallization from tert.-butyl methyl ether/methanol, 180 mg (90.1%) of 6-aminomethyl-3,7-dimethoxy-10-methyl-10H-dibenzo[b,e][1,4]oxazine-4-acetonitrile were obtained as a beige solid of m.p. 167°-169° (dec.).

Workup

  1. temperatureThe reaction mixture was heated to 85° for 4 hours
  2. temperaturethe cooled
  3. extractionThe aqueous phase was extracted with ethylene chloride
  4. dry with materialthe combined organic fractions were dried over magnesium chloride
  5. concentrationconcentrated
  6. customThe residue was dried in a high vacuum
  7. customafter recrystallization from tert.-butyl methyl ether/methanol

Sources & evidence

ORD record
ord-b3e37cefcb3b4bf494ce3bf8d7617c36
Source dataset
uspto-grants-1998_09
Patent number
US05811389

Reaction notes

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