tert-Butoxy bis(dimethylamino)methane → 6-[(Dimethylamino)methylene]-6,7,8,9-tetrahydro-9-(4-nitrobenzyl)-5H-pyrido[2,3-b]azepin-5-one

HRID 863030Notes

Reaction equation

HRID 863030 reaction equation
[N+:1]([C:4]1[CH:23]=[CH:22][C:7]([C:8]([N:10]2[CH2:16][CH2:15][CH2:14][C:13](=[O:17])[C:12]3[CH:18]=[CH:19][CH:20]=[N:21][C:11]2=3)=O)=[CH:6][CH:5]=1)([O-:3])=[O:2].C(O[CH:29](N(C)C)[N:30]([CH3:32])[CH3:31])(C)(C)C>O1CCCC1>[CH3:29][N:30]([CH:32]=[C:14]1[CH2:15][CH2:16][N:10]([CH2:8][C:7]2[CH:22]=[CH:23][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=2)[C:11]2[N:21]=[CH:20][CH:19]=[CH:18][C:12]=2[C:13]1=[O:17])[CH3:31]

Participants

4

Reactant 2

HCID 79885tert-Butoxy bis(dimethylamino)methaneHCID 196991276,7,8,9-tetrahydro-9-(4-nitrobenzoyl)-5H-pyrido[2,3-b]azepin-5-one

Product 1

HCID 676632686-[(Dimethylamino)methylene]-6,7,8,9-tetrahydro-9-(4-nitrobenzyl)-5H-pyrido[2,3-b]azepin-5-oneYield 90.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a slurry of 0.50 g of 6,7,8,9-tetrahydro-9-(4-nitrobenzoyl)-5H-pyrido[2,3-b]azepin-5-one in 10 ml of tetrahydrofuran under argon is added 0.70 g of tert-butoxy-bis(dimethylamino)methane and the mixture is stirred at room temperature overnight. The volatiles are removed under vacuum and the residue in ethyl acetate--CH2Cl2 (2:8) filtered through a short column of silica gel. The silica gel is washed with ethyl acetate (discard) and then with chloroform containing 3% methanol to give 0.51 g of the product as a yellow solid.

Workup

  1. customThe volatiles are removed under vacuum
  2. filtrationthe residue in ethyl acetate--CH2Cl2 (2:8) filtered through a short column of silica gel
  3. washThe silica gel is washed with ethyl acetate (discard)

Sources & evidence

ORD record
ord-9ee298d8487c459c835dd1f18e64edb3
Source dataset
uspto-grants-1998_02
Patent number
US05719278

Reaction notes

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