N-Iodosuccinimide → HCID 118036794, compound

HRID 1777909Notes

Reaction equation

HRID 1777909 reaction equation
[CH3:1][O:2][CH:3]([O:14][CH3:15])[C:4]1[N:13]=[C:12]2[C:7]([CH2:8][CH2:9][CH2:10][NH:11]2)=[CH:6][CH:5]=1.C1C(=O)N([I:23])C(=O)C1.[Al]>CC#N>[CH3:15][O:14][CH:3]([O:2][CH3:1])[C:4]1[N:13]=[C:12]2[C:7]([CH2:8][CH2:9][CH2:10][NH:11]2)=[CH:6][C:5]=1[I:23]

Participants

5

Reactant 3

HCID 120273N-IodosuccinimideHCID 5359268AluminumHCID 177501767-(Dimethoxymethyl)-1,2,3,4-tetrahydro-1,8-naphthyridine2×

Product 1

HCID 118036794HCID 118036794, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 7-(dimethoxymethyl)-1,2,3,4-tetrahydro-1,8-naphthyridine (intermediate 4, 1 g, 4.8 mmol) in MeCN (15 ml) was treated with NIS (1.13 g, 5.04 mmol), stirred for 4 h in a flask covered with aluminum foil. Them, the reaction mixture was concentrated. The residue was treated with Et2O and DCM, washed with water (2×) and brine, dried over Na2SO4, filtered and concentrated.

Workup

  1. concentrationThem, the reaction mixture was concentrated
  2. additionThe residue was treated with Et2O and DCM
  3. washwashed with water (2×) and brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-1d23fc12aa7e4d85a8e042abb9f949c3
Source dataset
uspto-grants-2016_02
Patent number
US09266883B2

Reaction notes

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