Dichloromethane → HCID 178523562, compound

HRID 1075753Notes

Reaction equation

HRID 1075753 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 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 filtration, 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-napthyridine-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
  9. filtrationby filtration
  10. filtrationThe precipitated crystals were collected by filtration
  11. washwashed with water
  12. customdried

Sources & evidence

ORD record
ord-59d62368a0d643f7a48eed93af6b418d
Source dataset
uspto-grants-1976_05
Patent number
US03954733

Reaction notes

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