Dichloromethane → HCID 178523562, compound

HRID 1415111Notes

Reaction equation

HRID 1415111 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:10]([OH:12])=[O:11])[NH2:9])=[CH:4][CH:3]=1.ClCCl.C[Si](C)(C)Cl.Cl.[OH:22][C:23]1[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][N:31]=2)[N:26]=[CH:25][C:24]=1[C:33](Cl)=[O:34]>C(N(CC)CC)C>[OH:22][C:23]1[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][N:31]=2)[N:26]=[CH:25][C:24]=1[C:33]([NH:9][CH:8]([C:5]1[CH:4]=[CH:3][C:2]([OH:1])=[CH:7][CH:6]=1)[C:10]([OH:12])=[O:11])=[O:34]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 6397ChlorotrimethylsilaneHCID 921434-HydroxyphenylglycineHCID 178479697HCID 178479697, compound

Product 1

HCID 178523562HCID 178523562, compound

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

To a mixture of 1.35 g of DL-2-p-hydroxyphenylglycine, 50 ml of anhydrous dichloromethane and 4.05 g of triethylamine, 2.62 g of trimethylchlorosilane were added, and the resulting mixture was refluxed for 20 minutes. After the addition of 2.1 g of 4-hydroxy-1,5-naphthyridine-3-carbonyl chloride hydrochloride, the reaction was effected while cooling with ice for 4 hours. The reaction mixture was concentrated under reduced pressure, 50 ml of water were added to the residue, and the resulting mixture was adjusted to pH 1 with 4N hydrochloric acid. The precipitated crystals were collected by filtration, suspended in 50 ml of water and potassium carbonate was added thereto. After removal of insoluble materials by filtratior, the filtrate was adjusted to pH 1. The precipitated crystals were collected by filtration, washed with water and dried to give 2.1 g of DL-α-(4-hydroxy-1,5-naphthyridine-3-carboxamido)-p-hydroxyphenylacetic acid. M.P. 310° to 320° C (decomp.).

Workup

  1. additionwere added
  2. temperaturethe resulting mixture was refluxed for 20 minutes
  3. temperaturewhile cooling with ice for 4 hours
  4. concentrationThe reaction mixture was concentrated under reduced pressure, 50 ml of water
  5. additionwere added to the residue
  6. filtrationThe precipitated crystals were collected by filtration
  7. additionpotassium carbonate was added
  8. customAfter removal of insoluble materials by filtratior
  9. filtrationThe precipitated crystals were collected by filtration
  10. washwashed with water
  11. customdried

Sources & evidence

ORD record
ord-3e4e8b02587442cb8c518cff61069e57
Source dataset
uspto-grants-1977_01
Patent number
US04003887

Reaction notes

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