Hydrochloric Acid → N-(5-Bromonaphthalene-1-carbonyl)-N-methylglycine

HRID 247197Notes

Reaction equation

HRID 247197 reaction equation
C[O:2][C:3](=[O:20])[CH2:4][N:5]([C:7]([C:9]1[C:18]2[C:13](=[C:14]([Br:19])[CH:15]=[CH:16][CH:17]=2)[CH:12]=[CH:11][CH:10]=1)=[O:8])[CH3:6].[OH-].[Na+].Cl>CO>[Br:19][C:14]1[CH:15]=[CH:16][CH:17]=[C:18]2[C:13]=1[CH:12]=[CH:11][CH:10]=[C:9]2[C:7]([N:5]([CH3:6])[CH2:4][C:3]([OH:20])=[O:2])=[O:8]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 13318008HCID 13318008, compound

Product 1

HCID 13318015N-(5-Bromonaphthalene-1-carbonyl)-N-methylglycineYield 91.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

N-[(5-Bromo-1-naphthalenyl)carbonyl]-N-methylglycine methyl ester (3.7 g, 11.0 mmoles, described in Example 2) was suspended in methanol (50 ml). A solution of 1N aqueous NaOH (13.2 ml) was added to the suspension. The mixture was stirred at 20°-22° C. for 1.5 hr. The mixture was neutralized with aqueous HCl and concentrated under reduced pressure to remove the methanol. The residual solution was made acidic with aqueous HCl and extracted with ethyl acetate. The extract was dried (MgSO4), filtered and evaporated to dryness. The residue was crystallized from ethanol-water to give 3.25 g of the title compound; mp 205° C.; NMR (DMSO-d6) δ 2.75 & 3.10 (2s, 3H), 2.75 & 3.10 (2s, 3H), 3.75 & 4.25 (2s, 2H), 7.3-8.3 (m, 6H); IR (Nujol*) 1745 with inflection at 1720, 1580 cm-1 ; UV λmax (EtOH) 322 nm (ε 680), 316 (1,000), 299 (6,510), 289 (9,055), 279 (7,150) 226 (63,080); Anal Calcd: C, 52.19% H, 3.76% N, 4.35%; Found: C, 52.09% H, 38.4% N, 4.48%.

Workup

  1. concentrationconcentrated under reduced pressure
  2. customto remove the methanol
  3. extractionextracted with ethyl acetate
  4. dry with materialThe extract was dried (MgSO4)
  5. filtrationfiltered
  6. customevaporated to dryness
  7. customThe residue was crystallized from ethanol-water

Sources & evidence

ORD record
ord-71a7d1610bcf4a53998438f33412e256
Source dataset
uspto-grants-1987_11
Patent number
US04705882

Reaction notes

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