Nitric Acid → trans-N-(7-chloro-8-nitro-2,3,4,14b-tetrahydro-1H-dibenzo[b,f]pyrido[1,2-d][1,4]oxazepin-1-yl)-2,2,2-trifluoroacetamide

HRID 16165Notes

Reaction equation

HRID 16165 reaction equation
[N+:1]([O-:4])(O)=[O:2].[Cl:5][C:6]1[CH:31]=[CH:30][C:9]2[O:10][C:11]3[CH:29]=[CH:28][CH:27]=[CH:26][C:12]=3[C@@H:13]3[C@H:18]([NH:19][C:20](=[O:25])[C:21]([F:24])([F:23])[F:22])[CH2:17][CH2:16][CH2:15][N:14]3[C:8]=2[CH:7]=1>C(Cl)Cl>[Cl:5][C:6]1[C:31]([N+:1]([O-:4])=[O:2])=[CH:30][C:9]2[O:10][C:11]3[CH:29]=[CH:28][CH:27]=[CH:26][C:12]=3[C@@H:13]3[C@H:18]([NH:19][C:20](=[O:25])[C:21]([F:24])([F:23])[F:22])[CH2:17][CH2:16][CH2:15][N:14]3[C:8]=2[CH:7]=1

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 86599857trans-N-(7-chloro-2,3,4,14b-tetrahydro-1H-dibenzo[b,f]pyrido[1,2-d][1,4]oxazepin-1-yl)-2,2,2-trifluoroacetamide

Product 1

HCID 86599874trans-N-(7-chloro-8-nitro-2,3,4,14b-tetrahydro-1H-dibenzo[b,f]pyrido[1,2-d][1,4]oxazepin-1-yl)-2,2,2-trifluoroacetamideYield 93.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Nitric acid (50 μL, 1.10 mmol) was added at 0° C. to a suspension of trans-N-(7-chloro-2,3,4,14b-tetrahydro-1H-dibenzo[b,f]pyrido[1,2-d][1,4]oxazepin-1-yl)-2,2,2-trifluoroacetamide (210 mg, 0.53 mmol) in 4 mL of CH2Cl2. After stirring the mixture was extracted with ethyl acetate and the organic layer was washed with 5% aq. sodium bicarbonate, dried (Na2SO4) and evaporated to give trans-N-(7-chloro-8-nitro-2,3,4,14b-tetrahydro-1H-dibenzo[b,f]pyrido[1,2-d][1,4]oxazepin-1-yl)-2,2,2-trifluoroacetamide (219 mg, 90%). Data: 1H-NMR (400 MHz, DMSO) 1.64-1.94 (m, 3H), 2.05 (br, 1H), 3.26 (t, J=8.0, 1H), 4.20 (d, J=8.0, 1H), 4.35 (d, J=8.0, 1H), 4.60 (dq, J=8.0, 3.0, 1H) 7.15 (m, 1H), 7.11-9.21 (6 ArH). (m/z)=443 (M+H)+.

Workup

  1. extractionwas extracted with ethyl acetate
  2. washthe organic layer was washed with 5% aq. sodium bicarbonate
  3. dry with materialdried (Na2SO4)
  4. customevaporated

Sources & evidence

ORD record
ord-69e4cfe623bb4f2e8bdedd6e06137f69
Source dataset
uspto-grants-2010_06
Patent number
US07737136B2

Reaction notes

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