Acetic Acid → HCID 470687, compound

HRID 724971Notes

Reaction equation

HRID 724971 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH3:31])[C:7](=[O:30])[C:8]3[CH:18]=[C:17]([CH2:19]NC4C=CC=C([N+]([O-])=O)C=4)[CH:16]=[N:15][C:9]=3[N:10]([CH2:13][CH3:14])[C:11]=2[N:12]=1.[OH-].[Na+].[C:34]([OH:37])(=O)[CH3:35]>Cl>[NH2:6][C:5]1[CH:11]=[C:34]([O:37][CH2:19][C:17]2[CH:16]=[N:15][C:9]3[N:10]([CH2:13][CH3:14])[C:11]4[N:12]=[C:2]([Cl:1])[CH:3]=[CH:4][C:5]=4[N:6]([CH3:31])[C:7](=[O:30])[C:8]=3[CH:18]=2)[CH:35]=[CH:3][CH:4]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 159563362-chloro-5,11-dihydro-11-ethyl-5-methyl-8-(3-nitrophenylamino)methyl-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one

Product 1

HCID 470687HCID 470687, compound

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

The 2-chloro-5,11-dihydro-11-ethyl-5-methyl-8-(3-nitrophenylamino)methyl-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one (0.080 g, 0.18 mmol) was dissolved in acetic acid (5 mL) and treated with a solution of stannous chloride dihydrate (0.154 g, 0.68 mmol) in concentrated hydrochloric acid (2 mL). After stirring for 17 hours the resulting mixture was made alkaline with 50% aqueous sodium hydroxide and extracted with dichloromethane (8×20 mL). The combined organics were dried over sodium sulfate, concentrated and the residue was purified by flash chromatography (hexanes to 1:1 hexanes/ethyl acetate gradient) to the title compound (0.046 g, 62%), m.p. 148°-149° C.

Workup

  1. extractionextracted with dichloromethane (8×20 mL)
  2. dry with materialThe combined organics were dried over sodium sulfate
  3. concentrationconcentrated
  4. customthe residue was purified by flash chromatography (hexanes to 1:1 hexanes/ethyl acetate gradient) to the title compound (0.046 g, 62%), m.p. 148°-149° C.

Sources & evidence

ORD record
ord-40366cea35de4f17a4d2e0754c87fad4
Source dataset
uspto-grants-1998_01
Patent number
US05705499

Reaction notes

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