Acetamidine monohydrochloride → 6,7-dihydro-2-methyl-7-(4-nitrobenzoyl)-5H-pyrimido[5,4-d][l]benzazepine

HRID 355866

Reaction equation

HRID 355866 reaction equation
Cl.[C:2]([NH2:5])(=[NH:4])[CH3:3].O(C)[Na].CN([CH:12]=[C:13]1[C:19](=O)[C:18]2[CH:21]=[CH:22][CH:23]=[CH:24][C:17]=2[N:16]([C:25](=[O:35])[C:26]2[CH:31]=[CH:30][C:29]([N+:32]([O-:34])=[O:33])=[CH:28][CH:27]=2)[CH2:15][CH2:14]1)C>CO>[CH3:3][C:2]1[N:4]=[CH:12][C:13]2[CH2:14][CH2:15][N:16]([C:25](=[O:35])[C:26]3[CH:27]=[CH:28][C:29]([N+:32]([O-:34])=[O:33])=[CH:30][CH:31]=3)[C:17]3[CH:24]=[CH:23][CH:22]=[CH:21][C:18]=3[C:19]=2[N:5]=1

Participants

5

Reactant 3

HCID 67170Acetamidine monohydrochlorideHCID 536535644-[(dimethylamino)methylene]-1,2,3,4-tetrahydro-1-(4-nitrobenzoyl)-5H-1-benzazepin-5-oneHCID 178418582HCID 178418582, compound

Product 1

HCID 543797936,7-dihydro-2-methyl-7-(4-nitrobenzoyl)-5H-pyrimido[5,4-d][l]benzazepineYield 99.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of 0.233 g of acetamidine hydrochloride in 36 ml of methyl alcohol under argon is added 0.133 g of NaOCH3. After 5 minutes, 0.600 g of 4-[(dimethylamino)methylene]-1,2,3,4-tetrahydro-1-(4-nitrobenzoyl)-5H-1-benzazepin-5-one is added and stirring continued for 18 hours. The volatiles are evaporated to a residue which is dissolved in ethyl acetate and passed through a pad of silica gel. The filtrate is evaporated in vacuo to is give 590 mg of the desired product as tan crystals, m.p. 211°-212° C. HR FABMS: Exact mass (M+H):361.1295.

Workup

  1. waitcontinued for 18 hours
  2. customThe volatiles are evaporated to a residue which
  3. dissolutionis dissolved in ethyl acetate
  4. customThe filtrate is evaporated in vacuo

Sources & evidence

ORD record
ord-06be943289d54cc7b443c1db275ec851
Source dataset
uspto-grants-1998_11
Patent number
US05834461

Linked notes

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