Dimethylformamide → N1-(9H-9-Fluorenyl)-4-(benzyloxy)-5-methoxy-2-nitrobenzamide

HRID 1876825Notes

Reaction equation

HRID 1876825 reaction equation
CN(C=O)C.[C:6]([O:14][C:15]1[C:23]([O:24][CH3:25])=[CH:22][C:18]([C:19]([OH:21])=O)=[C:17]([N+:26]([O-:28])=[O:27])[CH:16]=1)(=O)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.S(Cl)(Cl)=O.[CH:33]1[C:45]2[CH:44]([NH2:46])[C:43]3[C:38](=[CH:39][CH:40]=[CH:41][CH:42]=3)[C:37]=2[CH:36]=[CH:35][CH:34]=1>C1C=CC=CC=1.C(N(CC)CC)C>[CH:33]1[C:45]2[CH:44]([NH:46][C:19](=[O:21])[C:18]3[CH:22]=[C:23]([O:24][CH3:25])[C:15]([O:14][CH2:6][C:7]4[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=4)=[CH:16][C:17]=3[N+:26]([O-:28])=[O:27])[C:43]3[C:38](=[CH:39][CH:40]=[CH:41][CH:42]=3)[C:37]=2[CH:36]=[CH:35][CH:34]=1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 10671Fluoren-9-amineHCID 24386Thionyl ChlorideHCID 594400844-Benzoyloxy-5-methoxy-2-nitro benzoic acid

Product 1

HCID 66881172N1-(9H-9-Fluorenyl)-4-(benzyloxy)-5-methoxy-2-nitrobenzamideYield 80.6%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 8471TriethylamineSolvent

Procedure

DMF was added to a stirred suspension of 4-benzoyloxy-5-methoxy-2-nitro benzoic acid (6) (0.500 mg, 1.65 mmol) and thionyl chloride (3 ml) in dry benzene (30 ml) and the stirring was continued for 6 h. The benzene was evaporated in vacuum and the resultant oil dissolved in dry THF (50 ml) and added dropwise over a period of 1 h to a stirred suspension of 9H-9-fluorenamine (326, 15.6 mmol) triethylamine (5 ml). After the completion of addition, the reaction mixture was brought to ambient temperature and stirred for an additional hour. The THF was evaporated in vacuum and the aqueous layer was washed with ethyl acetate. The aqueous phase was then adjusted to pH 3 using 6 N HCl and extracted with ethyl acetate and washed with brine, dried over Na2SO4 and evaporated in vacuum to afford the crude product of (7e) (620 mg in 80% yield). 1H NMR (CDCl3) δ 3.95 (s, 3H), 5.20 (s, 2H), 5.70 (s, 1H), 6.70 (s, 1H), 7.00-7.41 (m, 5H), 7.45-7.706 (m, 9H); FABMS: 466 (M+H)+.

Workup

  1. customThe benzene was evaporated in vacuum
  2. dissolutionthe resultant oil dissolved in dry THF (50 ml)
  3. additionAfter the completion of addition
  4. customwas brought to ambient temperature
  5. customThe THF was evaporated in vacuum
  6. washthe aqueous layer was washed with ethyl acetate
  7. extractionextracted with ethyl acetate
  8. washwashed with brine
  9. dry with materialdried over Na2SO4
  10. customevaporated in vacuum

Sources & evidence

ORD record
ord-a19ff5ec1ceb41c4bbc0e9b9a264c368
Source dataset
uspto-grants-2012_11
Patent number
US08309726B2

Reaction notes

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