Methanol → 5-(4-aminobenzoyl)-1-ethoxycarbonylmethyl-1,3,4,5-tetrahydro-1,5-benzodiazepin-2(2H)-one

HRID 441220ノート

反応式

HRID 441220 の反応式
[CH2:1]([O:3][C:4]([CH2:6][N:7]1[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[N:11]([C:18](=[O:28])[C:19]2[CH:24]=[CH:23][C:22]([N+:25]([O-])=O)=[CH:21][CH:20]=2)[CH2:10][CH2:9][C:8]1=[O:29])=[O:5])[CH3:2].CO>[Fe].C(O)(=O)C>[NH2:25][C:22]1[CH:23]=[CH:24][C:19]([C:18]([N:11]2[C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[N:7]([CH2:6][C:4]([O:3][CH2:1][CH3:2])=[O:5])[C:8](=[O:29])[CH2:9][CH2:10]2)=[O:28])=[CH:20][CH:21]=1

参加物

5

反応物 2

HCID 887MethanolHCID 106684941-ethoxycarbonylmethyl-5-(4-nitrobenzoyl)-1,3,4,5-tetrahydro-1,5-benzodiazepin-2(2H)-one

生成物 1

HCID 104992005-(4-aminobenzoyl)-1-ethoxycarbonylmethyl-1,3,4,5-tetrahydro-1,5-benzodiazepin-2(2H)-one収率 98.9%

試薬・触媒・溶媒 2

HCID 23925Iron触媒HCID 176Acetic Acid溶媒

実験手順

The mixture of 1-ethoxycarbonylmethyl-5-(4-nitrobenzoyl)-1,3,4,5-tetrahydro-1,5-benzodiazepin-2(2H)-one (667 mg), iron powder (469 mg), methanol (10 ml) and acetic acid (1 ml) was refluxed for 1 hour. The reaction mixture was cooled to ambient temperature and it was filtered through a bed of celite followed by the removal of methanol. The residue was diluted with chloroform and to the mixture was added saturated sodium bicarbonate aqueous solution followed by stirring for 10 minutes. The resulting mixture was filtered through a bed of celite and the organic layer was washed with brine. Drying the filtrate, and the removal of chloroform obtained a crude product. The crude product was triturated with a mixture of diisopropyl ether and n-hexane (1:1) to give 5-(4-aminobenzoyl)-1-ethoxycarbonylmethyl-1,3,4,5-tetrahydro-1,5-benzodiazepin-2(2H)-one (610 mg) as a slightly brown powder.

後処理

  1. temperaturewas refluxed for 1 hour
  2. filtrationit was filtered through a bed of celite
  3. customfollowed by the removal of methanol
  4. additionThe residue was diluted with chloroform and to the mixture
  5. additionwas added saturated sodium bicarbonate aqueous solution
  6. filtrationThe resulting mixture was filtered through a bed of celite
  7. washthe organic layer was washed with brine
  8. customDrying the filtrate
  9. customthe removal of chloroform
  10. customobtained a crude product
  11. customThe crude product was triturated with a mixture of diisopropyl ether and n-hexane (1:1)

出典と根拠

ORDレコード
ord-963f6592c1d4418eb6492f2dc72f6b6e
出典データセット
uspto-grants-1996_05
特許番号
US05521170

反応ノート

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