Acetic Acid → 7-Bromo-1,2,4,5-tetrahydro-pyrido[2,3-e][1,4]diazepin-3-one

HRID 1362359Notes

Reaction equation

HRID 1362359 reaction equation
[NH:1]1[C:7]2[N:8]=[CH:9][CH:10]=[CH:11][C:6]=2[CH2:5][NH:4][C:3](=[O:12])[CH2:2]1.C(O)(=O)C.[Br:17]Br>CCCCCC>[Br:17][C:10]1[CH:9]=[N:8][C:7]2[NH:1][CH2:2][C:3](=[O:12])[NH:4][CH2:5][C:6]=2[CH:11]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 24408BromineHCID 592775691H,2H,3H,4H,5H-pyrido[2,3-e][1,4]diazepin-3-one

Product 1

HCID 592776207-Bromo-1,2,4,5-tetrahydro-pyrido[2,3-e][1,4]diazepin-3-one

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

1,2,4,5-Tetrahydro-pyrido[2,3-e][1,4]diazepin-3-one (164 mg, 1.0 mmol) was dissolved into acetic acid (1 mL). Bromine (160 mg, 1.0 mmol) was added dropwise at room temperature and the solution was stirred overnight. Hexane (5 mL) was added and the orange precipitate was filtered and dried in vacuo. The title compound was isolated as an orange solid (190 mg, 78%). 1H NMR (300 MHz, DMSO-d6) δ 8.26 (t, J=5.7 Hz, 1H), 8.06 (d, J=2.1 Hz, 1H), 7.81 (d, J=2.1 Hz, 1H), 4.35 (d, J=5.7 Hz, 2H), 4.08 (s, 2H).

Workup

  1. filtrationthe orange precipitate was filtered
  2. customdried in vacuo

Sources & evidence

ORD record
ord-54529094ddf447a5a00e47eeea3b1bb0
Source dataset
uspto-grants-2011_02
Patent number
US07879872B2

Reaction notes

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